Radical Reduction of Aromatic Azides to Amines. with Triethylsilane
|
|
|
- Cynthia Sullivan
- 5 years ago
- Views:
Transcription
1 adical eduction of Aromatic Azides to Amines with Triethylsilane Luisa Benati, Giorgio Bencivenni, ino Leardini, Matteo Minozzi,* Daniele Nanni,* osanna Scialpi, Piero Spagnolo,* and Giuseppe Zanardi Dipartimento di Chimica Organica "A. Mangini", Università di Bologna, Viale isorgimento 4, I Bologna, Italy Supporting information Table of contents: Page S2. General Procedure for the Preparation of Azides 1a-u. Page S3. General Procedure for the Preparation of Azides 4a-c. Pages S4-S5. GC-MS Spectra of anilinosilanes 2a-u. Page S6. GC-MS Spectra of alkylaminosilanes 5a-c. Page S7. eaction of Azide 1a in C 6 D 5 CD 3. S1
2 General Procedure for the Preparation of Azides 1a-u. The already known aryl azides 1a-u were prepared by diazotization of the corresponding anilines 3a-u, all commercially available, followed by treatment with sodium azide, according to a standard procedure. 1 All the azides were characterized on the basis of physical and/or spectral data (1a, 2 1b, 2 1c, 2 1d, 3 1e, 2 1f, 4 1g, 5 1h, 6 1i, 7 1j, 8 1k, 5 1l, 9 1m, 10 1n, 9 1o, 2 1p, 7 1q, 11 1r, 12 1s, 9 1t, 13 1u 14 ). 1a: = OMe 1g: = Br 1m: =OMe 1o: = OMe 1t 1b: = Me 1h: = I 1n: = Cl 1p: = Me 1c: = H 1i: = COMe 1q: = Ph 1d: = CN 1j: = COOMe 1r: = F 1u 1e: = F 1k: = COOH 1s: = Cl 1f: = Cl 1l: = NO 2 1 Smith, P. A. S.; Brown, B. B. J. Am. Chem. Soc. 1951, 73, Huber, M. L.; Pinhey, J. T. J. Chem. Soc. Perkin Trans , Nicolaides, A.; Enyo, T.; Miura, D.; Tomioka, H. J. Am. Chem. Soc. 2001, 123, Butler,. N.; Collier, S.; Fleming, A. F. M. J. Chem. Soc. Perkin Trans , Liu, Q.; Tor, Y. Org. Lett. 2003, 5, Hideo, T; Shinji, S. Org. Biomol. Chem. 2003, 1, Morawietz, J.; Sander, W.; Traeubel, M. J. Org. Chem. 1995, 60, Wollman, E. W.; Kang, D.; Frisbie, C. D.; Lorkovic, I. M.; Wrighton, M. S. J. Am. Chem. Soc. 1994, 116, Lieber, E.; amachandra,. C. N.; Chao T. S.; Hoffman, C. W. W. Anal. Chem. 1957, 29, Nunno, L. D.; Scilimati, A. Tetrahedron 1986, 42, Benati, L.; Montevecchi, P. C.; Spagnolo, P.; Foresti, E. J. Chem. Soc. Perkin Trans , Leyva, E.; Munoz, D.; Platz, M. S. J. Org. Chem. 1989, 54, Klump, S. P.; Shechter, H. Tetrahedron Lett. 2002, Forster, M. O.; Fierz, H. E. J. Chem. Soc 1907, S2
3 General Procedure for the Preparation of Azides 4a-c. The already known alkyl azides 4a-c were prepared from the corresponding commercially available bromo-derivatives. An acetone / water (25 ml / 25 ml) solution of the halogenated compound (2 mmol) and sodium azide (6 mmol) was stirred at room temperature until disappearance of the starting reagent. The acetone was removed at reduced pressure and the residue extracted with diethyl ether. Purification on silica-gel using a hexane / diethyl ether (90:10) mixture gave the pure azide in nearly quantitative yield (4a, 15 4b, 16 4c 17 ). Br Na (3 equiv) acetone / water 4a-c a: = PhCH 2 CH 2 b: = CH 3 (CH 2 ) 9 c: = NC(CH 2 ) 3 15 Lee, L. V.; Mitchell, M. L.; Huang, S. J.; Fokin, V. V.; Sharpless, K. B.; Wong, C. H. J. Am.Chem. Soc. 2003, 125, anu, B. C.; Sarkar, A.; Chakraborty,.; J. Org. Chem. 1994, 59, Da os, T.; Prato, M.; Lucchini, V. J. Org. Chem. 2000, 65, S3
4 GC-MS Spectra of Anilinosilanes 2a-u. 2a: = OMe 2g: = Br 2m: =OMe 2o: = OMe 2t 2b: = Me 2h: = I 2n: = Cl 2p: = Me 2c: = H 2d: = CN 2i: 2j: = COMe = COOMe 2q: = Ph 2r: = F 2u 2e: = F 2k: = COOH 2s: = Cl 2f: = Cl 2l: = NO 2 4-methoxy-N-(triethylsilyl)benzenamine 2a: 18 m/z (rel. inten.) 237 (80), 208 (100), 180 (48), 152 (34). 4-methyl-N-(triethylsilyl)benzenamine 2b: 18 m/z (rel. inten.) 221 (50), 192 (100), 164 (41), 136 (27), 134 (17). N-(triethylsilyl)benzenamine 2c: 18 m/z (rel. inten.) 207 (33), 178 (100), 150 (50), 122 (37), 120 (28). 4-(triethylsilylamino)benzonitrile 2d: 18 m/z (rel. inten.) 232 (28), 203 (100), 175 (53), 147 (51), 145 (33). 4-fluoro-N-(triethylsilyl)benzenamine 2e: 18 m/z (rel. inten.) 225 (35), 196 (100), 168 (61), 140 (54), 138 (28). 4-chloro-N-(triethylsilyl)benzenamine 2f: 18 m/z (rel. inten.) 241 (39), 214 (34), 212 (100), 186 (20), 184 (56), 158 (16), 156 (50), 154 (18). 1-(4-(triethylsilylamino)phenyl)ethanone 2i: m/z (rel. inten.) 249 (44), 220 (100), 192 (34). methyl 4-(triethylsilylamino)benzoate 2j: m/z (rel. inten.) 265 (40), 236 (100), 208 (32), 180 (14). 4-(triethylsilylamino)benzoic acid 2k: m/z (rel. inten.) 251 (6), 222 (100), 178 (15), 150 (25), 120 (63). S4
5 4-nitro-N-(triethylsilyl)benzenamine 2l: 18 m/z (rel. inten.) 252 (22), 223 (100), 195 (37), 167 (28), 120 (12). 3-methoxy-N-(triethylsilyl)benzenamine 2m: m/z (rel. inten.) 237 (49), 208 (100), 180 (50), 152 (23), 150 (17). 3-chloro-N-(triethylsilyl)benzenamine 2n: 18 m/z (rel. inten.) 241 (34), 212 (100), 184 (52), 156 (52). 2-methoxy-N-(triethylsilyl)benzenamine 2o: m/z (rel. inten.) 237 (21), 208 (18), 193 (100), 164 (37), 136 (12), 135 (12). 2-methyl-N-(triethylsilyl)benzenamine 2p: 18 m/z (rel. inten.) 221 (39), 192 (100), 164 (30), 162 (16), 134 (17). 2-Phenyl-N-(triethylsilyl)benzenamine 2q: m/z (rel. inten.) 283 (38), 254 (100), 224 (34), 196 (33). 2-fluoro-N-(triethylsilyl)benzenamine 2r: m/z (rel. inten.) 225 (29), 196 (24), 168 (100), 140 (28). 2-chloro-N-(triethylsilyl)benzenamine 2s: 18 m/z (rel. inten.) 241 (28), 212 (100), 186 (20), 184 (60), 156 (44). N-(triethylsilyl)naphthalen-1-amine 2t: m/z (rel. inten.) 257 (44), 228 (100), 198 (20), 170 (30), 143 (13). N-(triethylsilyl)naphthalen-2-amine 2u: m/z (rel. inten.) 257 (62), 228 (100), 200 (44), 172 (19), 170 (21), 143 (22), 129 (30). 18 Ali, M.; Eaborn, C.; Walton, D.. M. J. Organomet. Chem. 1974, 78, 83. S5
6 GC-MS spectra for alkylaminosilanes 5a-c. Ph 9 NHSiEt NC 3 5a 5b 5c 3-phenyl-N-(triethylsilyl)propan-1-amine 5a: m/z (rel. inten.) 249 (16), 220 (100), 144 (35), 116 (45), 91 (25). N-(triethylsilyl)undecan-1-amine 5b: m/z (rel. inten.) 285 (4), 256 (100), 144 (47), 116 (10). 5-(triethylsilylamino)pentanenitrile 5c: m/z (rel. inten.) 183 (M , 100), 142 (35), 128 (44). S6
7 eaction of 4-Methoxyphenyl Azide 1a in C 6 D 5 CD 3. The reaction of 4-methoxyphenyl azide 1a was also performed in C 6 D 5 CD 3 solution; in such case, direct 1 H and 13 C NM analysis of the resulting reaction mixture monitored the virtually exclusive presence of 4-methoxy-N-(triethylsilyl)benzeneamine 2a 18 [ 1 H NM (400 MHz, C 6 D 5 CD 3 ) δ 0.55 (q, 6 H, J = 8.1 Hz), 0.97 (t, 9 H, J = 8.1 Hz), 2.83 (br s, 1 H), 3.41 (s, 3 H), 6.49 (part of AA BB system, 2 H, J = 8.9 Hz), 6.65 (part of AA BB system, 2 H, J = 8.9 Hz); 13 C NM (100 MHz, C 6 D 5 CD 3 ) δ 55.1, 115.1, 117.6, (C), 152.9(C)]. S7
Simple copper/tempo catalyzed aerobic dehydrogenation. of benzylic amines and anilines
Simple copper/tempo catalyzed aerobic dehydrogenation of benzylic amines and anilines Zhenzhong Hu and Francesca M. Kerton,* Department of Chemistry, Memorial University of Newfoundland, St. John s, NL,
Regioective Halogenation of 2-Substituted-1,2,3-Triazole via sp 2 C-H Activation
Regioective Halogenation of 2-Substituted-1,2,3-Triazole via sp 2 C-H Activation Qingshan Tian, Xianmin Chen, Wei Liu, Zechao Wang, Suping Shi, Chunxiang Kuang,* Department of Chemistry, Tongji University,
One-pot Synthesis of 1-Alkyl-1H-indazoles. Supporting Information
One-pot Synthesis of 1-Alkyl-1H-indazoles from 1,1-Dialkylhydrazones via Aryne Annulation ataliya A. Markina, Anton V. Dubrovskiy, and Richard C. Larock* Department of Chemistry, Iowa State University,
# Supplementary Material (ESI) for Chemical Communications # This journal is The Royal Society of Chemistry 2005
Electronic Supplementary Information for: (Z)-Selective cross-dimerization of arylacetylenes with silylacetylenes catalyzed by vinylideneruthenium complexes Hiroyuki Katayama,* Hiroshi Yari, Masaki Tanaka,
Iron-Catalyzed Alkylation of Alkenyl Grignard Reagents
Supporting Information for Iron-Catalyzed Alkylation of Alkenyl Grignard Reagents Gérard Cahiez,* Christophe Duplais and Alban Moyeux Laboratoire de Synthèse Organique Sélective et de Chimie Organométallique
Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007 Organocatalytic Asymmetric Sulfa-Michael Addition to α,β- Unsaturated Ketones Paolo Ricci, Armando Carlone, Giuseppe
Divergent Construction of Pyrazoles via Michael Addition of N-Aryl Hydrazones to 1,2-Diaza-1,3-dienes
Divergent Construction of Pyrazoles via Michael Addition of N-Aryl Hydrazones to 1,2-Diaza-1,3-dienes Serena Mantenuto, Fabio Mantellini, Gianfranco Favi,* and Orazio A. Attanasi Department of Biomolecular
Supporting information for. Synthesis of phenothiazines from cyclohexanones and. 2-aminobenzenethiols under transition-metal-free conditions
Supporting information for Synthesis of phenothiazines from cyclohexanones and 2-aminobenzenethiols under transition-metal-free conditions Yunfeng Liao, a Pengcheng Jiang, a Shanping Chen, a Fuhong Xiao,
Supporting Information
Palladium-Catalyzed Cascade Oxidantion/sp 2 C-H Acylation of Azoarenes with Aryl Methanes Feng Xiong, a Cheng Qian, b Dongen Lin, b Wei Zeng b,* and Xiaoxia Lu a,* a Chengdu Institute of Biology,CAS, Chengdu
Supporting Information. Copper-catalyzed cascade synthesis of benzimidazoquinazoline derivatives under mild condition
Supporting Information Copper-catalyzed cascade synthesis of benzimidazoquinazoline derivatives under mild condition Shan Xu, Juyou Lu and Hua Fu* Key Laboratory of Bioorganic Phosphorus Chemistry and
Copyright Wiley-VCH Verlag GmbH, D Weinheim, Angew. Chem
Copyright Wiley-VCH Verlag GmbH, D-69451 Weinheim, 2000. Angew. Chem. 2000. Supporting Information for Salen as Chiral Activator : Anti vs Syn Switchable Diastereoselection in the Enantioselective Addition
Supporting Information
Supporting Information B(C 6 F 5 ) 3 -catalyzed Regioselective Deuteration of Electronrich Aromatic and Heteroaromatic compounds Wu Li, Ming-Ming Wang, Yuya Hu and Thomas Werner* Leibniz-Institute of Catalysis
Catalyst-free chemoselective N-tert-butyloxycarbonylation of amines in water
SUPPORTING INFORMATION Catalyst-free chemoselective N-tert-butyloxycarbonylation of amines in water Sunay V. Chankeshwara and Asit K. Chakraborti* National Institute of Pharmaceutical Education and Research
p-toluenesulfonic Acid-Mediated 1,3-Dipolar Cycloaddition of
Supporting Information for: p-toluenesulfonic Acid-Mediated 1,3-Dipolar Cycloaddition of Nitroolefins with NaN 3 for Synthesis of 4-Aryl-NH-1,2,3-triazoles Xue-Jing Quan, Zhi-Hui Ren, Yao-Yu Wang, and
Supporting Information
Supporting Information Synthesis of N-Heteropolycyclic Compounds Including Quinazolinone Skeletons by Using Friedel-Crafts Alkylation Bu Keun Oh, Eun Bi Ko, Jin Wook Han* and Chang Ho Oh* Department of
Electronic Supplementary Information
Efficient aerobic oxidative synthesis of 2-aryl quinazolines via benzyl C-H bond amination catalyzed by 4-hydroxy-TEMPO Bing Han,* Chao Wang, Run-Feng Han, Wei Yu,* Xiao-Yong Duan, Ran Fang and Xiu-Long
Supporting Information. as the nitro source
Supporting Information Efficient ipso-nitration of arylboronic acids with iron nitrate as the nitro source Min Jiang, a,b Haijun Yang,* a,b Yong Li, a,b Zhiying Jia b and Hua Fu b a Beijing Key Laboratory
A General and Efficient 2-Amination of Pyridines and Quinolines
A General and Efficient 2-Amination of Pyridines and Quinolines Jingjun Yin,* Bangping Xiang,* Mark A. Huffman, Conrad E. Raab, and Ian W. Davies Department of Process Research, rck Research Laboratories,
Copper-Catalyzed Cascade Cycloamination of alpha-csp 3 -H Bond of N-Aryl Ketimines with Azides: Access to Quinoxalines. Supporting Information
Copper-Catalyzed Cascade Cycloamination of alpha-csp 3 -H Bond of N-Aryl Ketimines with Azides: Access to Quinoxalines Tengfei Chen, Xun Chen, Jun Wei, Dongen Lin *, Ying Xie, and Wei Zeng * School of
Supporting Information for
S 1 Supporting Information for Novel and Convenient Synthesis of Substituted Quinolines by Copper or PalladiumCatalyzed Cyclodehydration of 1-(2-Aminoaryl)-2-yn-1-ols Bartolo Gabriele,*, Raffaella Mancuso,
Palladium Catalyzed Iodofluorination of Alkenes using Fluoro-Iodoxole Reagent
Supporting Information Palladium Catalyzed Iodofluorination of Alkenes using Fluoro-Iodoxole Reagent Nadia O. Ilchenko, Miguel A. Cortés and Kálmán J. Szabó* Stockholm University, Arrhenius Laboratory,
Supporting Information for. Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of. 3,5-Disubstituted Pyridines: Mechanistic Studies
Supporting Information for Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of 3,5-Disubstituted Pyridines: Mechanistic Studies Ta-Hsien Chuang* a, Yu-Chi Chen b and Someshwar Pola
Supporting Information. for. Pd-catalyzed decarboxylative Heck vinylation of. 2-nitro-benzoates in the presence of CuF 2
Supporting Information for Pd-catalyzed decarboxylative Heck vinylation of 2-nitro-benzoates in the presence of CuF 2 Lukas J. Gooßen*, Bettina Zimmermann, Thomas Knauber Address: Department of Chemistry,
Supporting Information. An Efficient Synthesis of Optically Active Physostigmine from Tryptophan via Alkylative Cyclization
Supporting Information An Efficient Synthesis of Optically Active Physostigmine from Tryptophan via Alkylative Cyclization Michiaki, Kawahara, Atsushi Nishida, Masako Nakagawa* Faculty of Pharmaceutical
Supporting Materials. Experimental Section. internal standard TMS (0 ppm). The peak patterns are indicated as follows: s, singlet; d,
CuBr-Catalyzed Efficient Alkynylation of sp 3 C-H Bonds Adjacent to a itrogen Atom Zhiping Li and Chao-Jun Li* Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec H3A
Supporting Information. Efficient copper-catalyzed Michael addition of acrylic derivatives with primary alcohols in the presence of base
Supporting Information Efficient copper-catalyzed Michael addition of acrylic derivatives with primary alcohols in the presence of base Feng Wang, a Haijun Yang, b Hua Fu, b,c * and Zhichao Pei a * a College
Copper(II) Ionic Liquid Catalyzed Cyclization-Aromatization of. Hydrazones with Dimethyl Acetylenedicarboxylate: A Green Synthesis
Copper(II) Ionic Liquid Catalyzed Cyclization-Aromatization of Hydrazones with Dimethyl Acetylenedicarboxylate: A Green Synthesis of Fully Substituted Pyrazoles Shirin Safaei, Iraj Mohammadpoor-Baltork,*
Supporting Information
Supporting Information [Cp*IrCl 2 ] 2 catalysed indirect functionalisation of alcohols: ovel strategies for the synthesis of substituted indoles Simon Whitney, Ronald Grigg *, Andrew Derrick and Ann Keep
Supporting Information
Supporting Information Synthesis of Pyrido-fused Quinazolinone Derivatives via Copper-catalyzed Domino Reaction Meilin Liu, Miaomiao Shu, Chaochao Yao, Guodong Yin,* Dunjia Wang, and Jinkun Huang* Hubei
Supporting Information
Supporting Information Direct Synthesis of Benzimidazoles by Dehydrogenative Coupling of Aromatic Diamines and Alcohols Catalyzed by Cobalt Prosenjit Daw, Yehoshoa Ben-David, and David Milstein* Department
Supporting information
Supporting information Diversity Oriented Asymmetric Catalysis (DOAC): Stereochemically Divergent Synthesis of Thiochromanes Using an Imidazoline-aminophenol aminophenol (IAP)-Ni Catalyzed Michael/Henry
Preparation of Fluorinated Tetrahydropyrans and Piperidines using a New Nucleophilic Fluorination Reagent DMPU/HF
Supporting information Preparation of Fluorinated Tetrahydropyrans and Piperidines using a New Nucleophilic Fluorination Reagent DMPU/HF Otome E. Okoromoba, a Gerald B. Hammond, a, * Bo Xu b, * a Department
Electronic Supplementary Information (ESI)
Electronic Supplementary Information (ESI) Mild and convenient one-pot synthesis of 2-amino-1,3,4-oxadiazoles promoted by trimethylsilyl isothiocyanate (TMSNCS) Dinneswara Reddy Guda, Hyeon Mo Cho, Myong
Supporting Information Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C C Bond Cleavage of 2-Arylin
Supporting Information Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C C Bond Cleavage of 2-Arylindoles Wei-Li Chen, Si-Yi Wu, Xue-Ling Mo, Liu-Xu Wei,
Supplemental materials for:
Tambar and Stoltz, Supporting Information 1 Supplemental materials for: The Direct Acyl-Alkylation of Arynes Uttam K. Tambar and Brian M. Stoltz* The Arnold and Mabel Beckman Laboratories of Chemical Synthesis,
Arylation of α-pivalate Ketones via Ni-Catalyzed sp3 C-O Activation with Arylboroxine
Arylation of α-pivalate Ketones via Ni-Catalyzed sp3 C-O Activation with Arylboroxine Kun Huang, Gang Li, Wei-Ping Huang, Da-Gang Yu and Zhang-Jie Shi* Beijing National Laboratory of Molecular Sciences
Schwartz s reagent-mediated regiospecific synthesis of 2,3-disubstituted indoles from isatins
Electronic Supplementary Information (ESI) Schwartz s reagent-mediated regiospecific synthesis of 2,3-disubstituted indoles from isatins A. Ulikowski and B. Furman* Institute of Organic Chemistry, Polish
The First Au-Nanoparticles Catalyzed Green Synthesis of Propargylamines Via Three-Component Coupling Reaction of Aldehyde, Alkyne And Amine
Supporting information of The First Au-anoparticles Catalyzed Green Synthesis of Propargylamines Via Three-Component Coupling Reaction of Aldehyde, Alkyne And Amine Mazaahir Kidwai a *, Vikas Bansal a,
Electronic Supplementary Information. Quinine/Selectfluor Combination Induced Asymmetric Semipinacol Rearrangement of
Electronic Supplementary Information Quinine/Selectfluor Combination Induced Asymmetric Semipinacol Rearrangement of Allylic Alcohols: An Effective and Enantioselective Approach to α Quaternary β Fluoro
Ruthenium-Catalyzed C H Oxygenation on Aryl Weinreb Amides
Supporting Information Ruthenium-Catalyzed C H xygenation on Aryl Weinreb Amides Fanzhi Yang and Lutz Ackermann* Institut für rganische und Biomolekulare Chemie Georg-August-Universität Tammannstrasse
Supplementary Materials Contents
Supplementary Materials Contents Supporting information... S1 1. General Information & Materials... S2 2. General Procedure for ptimization of Amidation of Aryl Bromides with Copper/,-Dimethylglycine Catalytic
Supporting Information
Supporting Information Cobalt-Catalyzed Carbonylation of C(sp 2 )-H Bonds with Azodicarboxylate as the Carbonyl Source Jiabin Ni,, Jie Li,,š Zhoulong Fan,, and Ao Zhang *,,,š CAS Key Laboratory of Receptor
Preparation of Stable Aziridinium Ions and Their Ring Openings
Supplementary Information Preparation of Stable Aziridinium Ions and Their Ring Openings Yongeun Kim a Hyun-Joon Ha*, a Sae Young Yun b and Won Koo Lee,*,b a Department of Chemistry and Protein Research
Electronic Supplementary Information (ESI) belonging to
Electronic Supplementary Information (ESI) belonging to Highly modular access to functionalised metal-carbenes via post-modifications of a single bromoalkyl-substituted NHC Pd(II) complex Han Vinh Huynh,*
Support Information. Table of contents. Experimental procedures. S2. Spectroscopic data... S2-S23. Photophysical properties..
Support Information Regioselective 2,6-dihalogenation of BODIPYs in 1,1,1,3,3,3-hexafluoro-2-propanol and preparation of novel meso-alkyl polymeric BODIPY dyes Liang Wang a, Jian-Wei Wang a, Ai-jun Cui
Direct Aerobic Carbonylation of C(sp 2 )-H and C(sp 3 )-H Bonds through Ni/Cu Synergistic Catalysis with DMF as the Carbonyl Source
Direct Aerobic Carbonylation of C(sp 2 )-H and C(sp 3 )-H Bonds through Ni/Cu Synergistic Catalysis with DMF as the Carbonyl Source Xuesong Wu, Yan Zhao, and Haibo Ge* Table of Contents General Information...
Supporting Information for. Boronic Acid Functionalized Aza-Bodipy (azabdpba) based Fluorescence Optodes for the. analysis of Glucose in Whole Blood
Supporting Information for Boronic Acid Functionalized Aza-Bodipy (azabdpba) based Fluorescence Optodes for the analysis of Glucose in Whole Blood Yueling Liu, Jingwei Zhu, Yanmei Xu, Yu Qin*, Dechen Jiang*
Specific N-Alkylation of Hydroxypyridines Achieved by a Catalyst- and Base-Free Reaction with Organohalides
Supporting Information Specific N-Alkylation of Hydroxypyridines Achieved by a Catalyst- and Base-Free Reaction with Organohalides Bin Feng, Yang Li, Huan Li, Xu Zhang, Huamei Xie, Hongen Cao, Lei Yu,
Directed Ortho Lithiation of N-Alkylphenylaziridines
Directed rtho Lithiation of -Alkylphenylaziridines Vito Capriati, Saverio Florio,* Renzo Luisi, Biagia Musio Dipartimento Farmaco-Chimico, Università di Bari, Via E. rabona 4, I-70126 Bari, C..R., Istituto
Electronic Supplementary Information
Electronic Supplementary Information A Novel and Facile Zn-mediated Intramolecular Five-membered Cyclization of β-tetraarylporphyrin Radicals from β-bromotetraarylporphyrins Dong-Mei Shen, Chao Liu, Qing-Yun
Supporting Information
Supporting Information Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-Triazoles with 2,1-Benzisoxazoles or 1,2-Benzisoxazoles Xiaoqiang Lei, Mohan Gao, Yefeng Tang*,,, E-mail: yefengtang@tsinghua.edu.cn
A Hierarchy of Aryloxide Deprotection by Boron Tribromide. Supporting Information
A Hierarchy of Aryloxide Deprotection by Boron Tribromide Sreenivas Punna, Stéphane Meunier and M. G. Finn* Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute,
Supporting Information. Palladium-Catalyzed Formylation of Aryl Iodides with HCOOH as
Supporting Information Palladium-Catalyzed Formylation of Aryl Iodides with HCOOH as CO Source Guanglong Sun,,, Xue Lv,,, Yinan Zhang, Min Lei,*,, and Lihong Hu*, Jiangsu Key Laboratory for Functional
Improved Carbonylation of Heterocyclic Chlorides and Challenging Aryl Bromides
Albaneze-Walker et al S-1 Improved Carbonylation of Heterocyclic Chlorides and Challenging Aryl Bromides Jennifer Albaneze-Walker*, Charles Bazaral, Tanya Leavey, Peter G. Dormer, and Jerry A. Murry Department
Supporting Information
Supporting Information Wiley-VCH 2010 69451 Weinheim, Germany Direct, One-pot Sequential Reductive Alkylation of Lactams/Amides with Grignard and Organolithium Reagents through Lactam/Amide Activation**
Enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction
Enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction P. Veeraraghavan Ramachandran* and Prem B. Chanda Department of Chemistry, Purdue
Base-promoted acetal formation employing aryl salicylates
Base-promoted acetal formation employing aryl salicylates Pinmanee Boontheung, Patrick Perlmutter*, and Evaloni Puniani School of Chemistry, Monash University, PO Box 23, Victoria 3800 Australia E-mail:
ph Switchable and Fluorescent Ratiometric Squarylium Indocyanine Dyes as Extremely Alkaline Sensors
ph Switchable and Fluorescent Ratiometric Squarylium Indocyanine Dyes as Extremely Alkaline Sensors Jie Li, Chendong Ji, Wantai Yang, Meizhen Yin* State Key Laboratory of Chemical Resource Engineering,
Supplementary Information
Supplementary Information Ruthenium(IV) porphyrin catalyzed phosphoramidation of aldehyde with phosphoryl azide as nitrene source Wenbo Xiao, Cong-Ying Zhou and Chi-Ming Che* Department of Chemistry, State
Supporting Information. Bond Formation for Alkaloid Synthesis Using Aryl. Azides as Nitrogen Source
Supporting Information [e( 20 TPP)Cl] Catalyzed Intramolecular C Bond ormation for Alkaloid Synthesis Using Aryl Azides as itrogen Source Yungen Liu, Jinhu Wei and Chi-Ming Che* Department of Chemistry
SUPPORTING INFORMATION
SUPPORTING INFORMATION Exploiting the Ring Strain in Bicyclo[2.2.1]heptane Systems for the Stereoselective Preparation of Highly Functionalized Cyclopentene, Dihydrofuran, Pyrroline and Pyrrolidine Scaffolds
Chemo- and Enantioselective Rh-Catalyzed Hydrogenation of 3-Methylene-1,2-diazetidines: Application to Vicinal Diamine Synthesis
Chemo- and Enantioselective Rh-Catalyzed Hydrogenation of 3-Methylene-1,2-diazetidines: Application to Vicinal Diamine Synthesis Greg P. Iacobini, a David W. Porter, b and Michael Shipman* a a Department
Supporting Information. for. Access to pyrrolo-pyridines by gold-catalyzed. hydroarylation of pyrroles tethered to terminal alkynes
Supporting Information for Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes Elena Borsini 1, Gianluigi Broggini* 1, Andrea Fasana 1, Chiara Baldassarri
Supporting Information
Supporting Information An Amphiphilic Pillar[5]arene as Efficient and Substrate-Selective Phase-Transfer Catalyst Tomoki Ogoshi*, Naosuke Ueshima and Tada-aki Yamagishi Table of Contents Experimental Section
Self-organization of dipyridylcalix[4]pyrrole into a supramolecular cage for dicarboxylates
![Self-organization of dipyridylcalix[4]pyrrole into a supramolecular cage for dicarboxylates](/thumbs/94/118164746.jpg "Self-organization of dipyridylcalix[4]pyrrole into a supramolecular cage for dicarboxylates")
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information Self-organization of dipyridylcalix[4]pyrrole into a supramolecular
Supplementary Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Supplementary Information Oxidative Tandem Annulation of 1 (2 Ethynylaryl)prop 2 en 1 ones Catalyzed
Electronic Supplementary Information
Electronic Supplementary Information ~ Experimental Procedures and Spectral/Analytical Data ~ Use of Dimethyl Carbonate as a Solvent Greatly Enhances the Biaryl Coupling of Aryl Iodides and Organoboron
Electronic Supplementary Information
Michal Szostak, Malcolm Spain and David J. Procter* School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, United Kingdom david.j.procter@manchester.ac.uk Electronic Supplementary
1,5-Electrocyclization of conjugated azomethine ylides derived from 3-formyl chromene and N-alkyl amino acids/esters
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 7 Supporting Information for,5-electrocyclization of conjugated azomethine ylides
Supporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Supporting Information Facile Three-Step Synthesis and Photophysical Properties of [8]-, [9]-,
Lewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines
Supporting Information for Lewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines Yingle Liu a, Jiawang Liu
Transition Metal Free Intramolecular Selective Oxidative C(sp 3 )-N Coupling: Synthesis of N-Arylisoindolinones
Electronic Supplementary Material (ESI) for Chemical Communications. This journal is The Royal Society of Chemistry 2014 Supporting information for Transition Metal Free Intramolecular Selective xidative
Development of a near-infrared fluorescent probe for monitoring hydrazine in serum and living cells
Supporting Information for Development of a near-infrared fluorescent probe for monitoring hydrazine in serum and living cells Sasa Zhu, Weiying Lin,* Lin Yuan State Key Laboratory of Chemo/Biosensing
Three-component synthesis of α-branched amines under Barbier-like conditions
Three-component synthesis of α-branched amines under Barbier-like conditions Erwan Le Gall*, Caroline Haurena, Stéphane Sengmany, Thierry Martens and Michel Troupel Électrochimie et Synthèse Organique,
Cu-Catalyzed Direct C6-Arylation of Indoles
Cu-Catalyzed Direct C6-Arylation of Indoles (Supporting Information) Youqing Yang, Ruirui Li, Yue Zhao, Dongbing Zhao, and Zhuangzhi Shi*, State Key Laboratory of Coordination Chemistry, Collaborative
Supporting Information
Supporting Information De Novo Synthesis of Polysubstituted Naphthols and Furans Using Photoredox Neutral Coupling of Alkynes with 2-Bromo-1,3-Dicarbonyl Compounds Heng Jiang, Yuanzheng Cheng, Yan Zhang,*
Novel Aldosterone Synthase Inhibitors with Extended Carbocyclic Skeleton by a Combined Ligand-Based and Structure-Based Drug Design Approach
Supporting Information Novel Aldosterone Synthase Inhibitors with Extended Carbocyclic Skeleton by a Combined Ligand-Based and Structure-Based Drug Design Approach Simon Lucas, Ralf Heim, Matthias Negri,
Supplementary Figures
Supplementary Figures Supplementary Figure 1. 1 H NMR (400 MHz, CDCl3) spectrum of 3a Supplementary Figure 2. 13 C NMR (75 MHz, CDCl3) spectrum of 3a 1 Supplementary Figure 3. 1 H NMR (400 MHz, CDCl3)
Chiral Squaramide Derivatives are Excellent Hydrogen Bond Donor Catalysts. Jeremiah P. Malerich, Koji Hagihara, and Viresh H.
Chiral Squaramide Derivatives are Excellent ydrogen Bond Donor Catalysts Jeremiah P. Malerich, Koji agihara, and Viresh. Rawal* Department of Chemistry, University of Chicago, Chicago, Illinois 60637 E-mail:
Microwave heating in peptide side chain modification via sulfhydryl reaction
Microwave heating in peptide side chain modification via sulfhydryl reaction E. Calce and S. De Luca* Institute of Biostructures and Bioimaging, National Research Council, 80134 Naples, Italy stefania.deluca@cnr.it
Structure and conserved function of iso-branched sphingoid bases from the nematode Caenorhabditis elegans
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 207 Structure and conserved function of iso-branched sphingoid bases from the nematode Caenorhabditis
Nitro-Grela-type complexes containing iodides. robust and selective catalysts for olefin metathesis
Supporting Information for Nitro-Grela-type complexes containing iodides robust and selective catalysts for olefin metathesis under challenging conditions. Andrzej Tracz, 1,2 Mateusz Matczak, 1 Katarzyna
Supporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Supporting Information Enantioselective Cu-catalyzed 1,4-Addition of Various Grignard Reagents to Cyclohexenone using Taddol-derived Phosphine-Phosphite
Zn Mediated Regioselective Barbier Reaction of Propargylic Bromides in THF/aq. NH 4 Cl Solution
Molecules 2001, 6, 964-968 molecules ISSN 1420-3049 http://www.mdpi.org Zn Mediated egioselective Barbier eaction of Propargylic Bromides in TF/aq. N 4 Cl Solution Artur Jõgi and Uno Mäeorg* Institute
Pyridazine N-Oxides as Precursors of Metallocarbenes: Rhodium-Catalyzed Transannulation with Pyrroles. Supporting Information
Pyridazine N-Oxides as Precursors of Metallocarbenes: Rhodium-Catalyzed Transannulation with Pyrroles Vinaykumar Kanchupalli, Desna Joseph and Sreenivas Katukojvala* Department of Chemistry, Indian Institute
molecules ISSN
Molecules 2006, 11, 357-364 Full Paper molecules ISSN 1420-3049 http://www.mdpi.org Synthesis of Novel Sterically Demanding Carbo- and Heterocyclic β-ketoesters Marko D. Mihovilovic,* Thomas C. M. Fischer
CDI Mediated Monoacylation of Symmetrical Diamines and Selective Acylation of Primary Amines of Unsymmetrical Diamines
Supporting information: CDI Mediated Monoacylation of Symmetrical Diamines and Selective Acylation of Primary Amines of Unsymmetrical Diamines Sanjeev K. Verma*, Ramarao Ghorpade, Ajay Pratap and M. P.
3016 Oxidation of ricinoleic acid (from castor oil) with KMnO 4 to azelaic acid
6 Oxidation of ricinoleic acid (from castor oil) with KMnO 4 to azelaic acid CH -(CH ) OH (CH ) -COOH KMnO 4 /KOH HOOC-(CH ) -COOH C H 4 O (.) KMnO 4 KOH (.) (6.) C H 6 O 4 (.) Classification Reaction
Supplementary Material
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supplementary Material PhI(Ac) 2 -BF 3 -Et 2 Mediated Domino Imine Activation, Intramolecular
A Novel Synthesis of Arylpyrrolo[1,2-a]pyrazinone Derivatives
![A Novel Synthesis of Arylpyrrolo[1,2-a]pyrazinone Derivatives](/thumbs/77/74538875.jpg "A Novel Synthesis of Arylpyrrolo[1,2-a]pyrazinone Derivatives")
Molecules 2004, 9, 574-582 molecules ISS 1420-049 http://www.mdpi.org A ovel Synthesis of ylpyrrolo[1,2-a]pyrazinone Derivatives Fei Wang*, Jiawei Wang and Shoufang Zhang School of Pharmaceutical Engineering,
Supporting Information
Zinc-Mediated Addition of Diethyl Bromomalonate to Alkynes for the Cascade Reaction towards Polysubstituted Pyranones and Tetracarbonyl Derivatives Anne Miersch, Klaus Harms, and Gerhard Hilt* Fachbereich
Supporting Information: Copper-catalysed reductive amination of nitriles and organic-group reductions using dimethylamine borane
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information: Copper-catalysed reductive amination of nitriles and organic-group
Supporting Information. Palladium-catalyzed reductive cleavage of tosylated arene using isopropanol as the mild reducing agent
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2014 Supporting Information Supporting Information Palladium-catalyzed reductive cleavage
Conversion of Biomass-derived Fatty Acids and Derivatives. into Hydrocarbons Using a Meta-Free Hydrodeoxygenation. Process
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The oyal Society of Chemistry 2015 Supporting Information for : Conversion of Biomass-derived Fatty Acids and Derivatives into
Supporting Information. Use of Potassium. -Trifluoroborato Amides in Suzuki-Miyaura. Cross-Coupling Reactions
Supporting Information Use of Potassium -Trifluoroborato Amides in Suzuki-Miyaura Cross-Coupling Reactions Gary A. Molander* and Ludivine Jean-Gérard Roy and Diana Vagelos Laboratories, Department of Chemistry,
Supporting Information
Supporting Information Unconventional Passerini Reaction towards α-aminoxyamides Ajay L. Chandgude, Alexander Dömling* Department of Drug Design, University of Groningen, Antonius Deusinglaan 1, 9713 AV
Naoya Takahashi, Keiya Hirota and Yoshitaka Saga* Supplementary material
Supplementary material Facile transformation of the five-membered exocyclic E-ring in 13 2 -demethoxycarbonyl chlorophyll derivatives by molecular oxygen with titanium oxide in the dark Naoya Takahashi,
SUPPLEMENTARY INFORMATION
doi:10.1038/nature14875 Switching on Elusive rganometallic chanisms with Photoredox Catalysis Jack A. Terrett, James D. Cuthbertson, Valerie W. Shurtleff, and David W. C. MacMillan WWW.NATURE.CM/NATURE
Stereoselective Aza-Darzens Reactions of Tert- Butanesulfinimines: Convenient Access to Chiral Aziridines
Stereoselective Aza-Darzens Reactions of Tert- Butanesulfinimines: Convenient Access to Chiral Aziridines Toni Moragas Solá, a Ian Churcher, b William Lewis a and Robert A. Stockman* a Supplementary Information
Catalytic decarboxylative alkylation of β-keto acids with sulfonamides via the cleavage of carbon nitrogen and carbon carbon bonds
Catalytic decarboxylative alkylation of β-keto acids with sulfonamides via the cleavage of carbon nitrogen and carbon carbon bonds Cui-Feng Yang, Jian-Yong Wang and Shi-Kai Tian* Joint Laboratory of Green