Supporting Information. Use of Potassium. -Trifluoroborato Amides in Suzuki-Miyaura. Cross-Coupling Reactions
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1 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, University of Pennsylvania, Philadelphia, Pennsylvania Table of Contents General Considerations...S2 Preparation of Potassium -Trifluoroborato Amides... S2 Suzuki-Miyaura Cross-Coupling Reactions of Potassium -Trifluoroborato Amides and Aryl Chlorides S4 References...S15 MR Spectra...S16 S1
2 General considerations: Pd(Ac) 2, RuPhos (2-dicyclohexylphosphino-2,6 -diisopropoxybiphenyl) and SPhos (2-dicyclohexylphosphino-2,6 -dimethoxybiphenyl) were used as received. Standard benchtop techniques were employed for handling air sensitive reagents. THF and toluene were distilled from a/benzophenone ketyl. Methanol was distilled from magnesium methoxide. Distilled H 2 was degassed by sparging with 2 (g) for >30 min. All other solvents were HPLC grade and used as received. Melting points (ºC) are uncorrected. 1 H, 13 C, 11 B, and 19 F MR spectra were recorded at 500 MHz, MHz, MHz, and MHz, respectively. Analytical thin layer chromatography (TLC) was performed on silica gel aluminum plates (0.25 mm) precoated with a fluorescent indicator. Visualization was effected with ultraviolet light or vanillin. Standard flash chromatography procedures were followed using μm silica gel. Preparation of the Potassium -Trifluoroborato Amides: BF 3 K Potassium 3-Trifluoroborato-1-morpholinopropan-1-one (1b). This product was prepared from 4-acryloylmorpholine (1.0 g, 7.1 mmol) according to the general procedure to give a white solid in 57% yield (970 mg, 3.9 mmol): mp = ºC; 1 H-MR (300 MHz, DMS-d 6 ) (m, 4H), (m, 4H), 2.02 (m, 2H), 0.11 (m, 2H); 13 C-MR (125.8 MHz, D 2 ) major rotamer 178.2, 66.4, 66.3, 46.3, 42.0, 28.5, 13.4; 19 F MR (471 MHz, D 2 ) major rotamer (m); 11 B MR (128 MHz, D 2 ) 4.82 (br s); IR (KBr) 2974, 2917, 2894, 1637 cm -1 ; HRMS (ES-) m/z calcd. for C 7 H 12 BF 3 2 (M-K + ) , found BF 3 K Potassium 2-(Trifluoroboratomethyl)-,-dimethylpropanamide (1c). S2
3 This product was prepared from,-dimethylmethacrylamide (1.0 g, 8.8 mmol) according to the general procedure to give a white solid in 68% yield (1.3 g, 5.9 mmol): mp = ºC; 1 H-MR (500 MHz, DMS-d 6 ) 2.94 (s, 3H), 2.74 (s, 3H), 2.57 (m, 1H), 0.89 (d, J = 6.5 Hz, 3H), 0.18 (m, 1H), (m, 1H); 13 C-MR (125.8 MHz, DMS-d 6 ) 179.0, 36.5, 34.8, 31.8, 18.8; 19 F MR (471 MHz, DMS-d 6 ) (m); 11 B MR (128 MHz, DMS-d 6 ) 4.53 (br s); IR (KBr) 2964, 2931, 1625 cm - 1 ; HRMS (ES-) m/z calcd. for C 6 H 12 BF 3 (M-K + ) , found Ph H BF 3 K Potassium 3-Trifluoroborato--phenylpropanamide (1d). This product was prepared from -phenylacrylamide (1.0 g, 6.8 mmol) according to the general procedure to give a white solid in 98% yield (1.7 g, 6.6 mmol): mp = ºC; 1 H-MR (500 MHz, DMS-d 6 ) 9.56 (br s, 1), 7.60 (d, J = 7.5 Hz, 2H), 7.23 (t, J = 7.5 Hz, 2H), 6.96 (t, J = 7.5 Hz, 1H), 2.09 (m, 2H), 0.33 (m, 2H); 13 C-MR (125.8 MHz, DMS-d 6 ) 175.7, 140.1, 128.5, 122.4, 118.9, 34.3; 19 F MR (471 MHz, DMS-d 6 ) (m); 11 B MR (128 MHz, DMS-d 6 ) 4.52 (br s); IR (KBr) 3317, 1634 cm -1 ; HRMS (ES-) m/z calcd. for C 9 H 10 BF 3 (M-K + ) , found Me BF 3 K Potassium 3-Trifluoroborato-1-(4-fluorophenyl)propan-1-one (1e). This product was prepared from freshly made -methoxy--methylacrylamide 1 (656 mg, 5.7 mmol) according to the general procedure to give a white solid in 95% yield (1.2 g, 5.4 mmol): mp = ºC; 1 H-MR (500 MHz, D 2 ) major rotamer 3.49 (m, 3H), 2.92 (m, 3H), 2.10 (m, 2H), 0.20 (m, 2H); 13 C-MR (125.8 MHz, D 2 ) major rotamer 179.1, 61.3, 31.9, 26.7, 12.2; 19 F MR (471 MHz, D 2 ) S3
4 major rotamer (m); 11 B MR (128 MHz, DMS-d 6 ) 4.48 (br s); IR (KBr) 1638, 1235 cm -1 ; HRMS (ES-) m/z calcd. for C 5 H 10 BF 3 2 (M-K + ) , found H 2 BF 3 K Potassium 3-Trifluoroboratopropanamide (1f). This product was prepared from acrylamide (355.4 mg, 5.0 mmol) according to the general procedure to give a white solid in 55% yield (495 mg, 2.75 mmol): mp > 200 ºC; 1 H-MR (500 MHz, DMS-d 6 ) 6.91 (br s, 1H), 6.32 (br s, 1H), 1.84 (m, 2H), 0.19 (m, 2H); 13 C-MR (125.8 MHz, DMS-d 6 ) 179.0, 32.8; 19 F MR (471 MHz, DMS-d 6 ) (m); 11 B MR (128 MHz, DMS-d 6 ) 4.70 (br s); IR (KBr) 3475, 2923, 2911, 1640 cm -1 ; HRMS (ES-) m/z calcd. for C 3 H 6 BF 3 (M-K + ) , found Suzuki-Miyaura Cross-Coupling Reactions of Potassium -Trifluoroborato Amides and Aryl Electrophiles: METHD A C 3-(4-Cyanophenyl)-,-dimethylpropanamide (3a). To a mixture of potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol), 4- chlorobenzonitrile (34.4 mg, 0.25 mmol), K 2 C 3 (103.7 mg, 0.75 mmol), Pd(Ac) 2 (2.8 mg, mmol) and RuPhos (11.7 mg, mmol) under nitrogen was added toluene/h 2 (5:1, 1.2 ml). The reaction was heated at 85 ºC with stirring under a nitrogen atmosphere for 14 h and then cooled to rt. A solution of ph 7 buffer (4.0 ml) was added, and the resulting mixture was extracted with EtAc (3 3 ml). The organic layer was dried (MgS 4 ) and then filtered. The solvent was removed in vacuo and the crude product was purified by silica gel chromatography to afford the desired compound as a white solid S4
5 in 81% yield (40.8 mg, 0.20 mmol): mp = ºC; 1 H-MR (500 MHz, CDCl 3 ) 7.57 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 8.0 Hz, 2H), 3.04 (t, J = 7.6 Hz, 2H), 2.97 (s, 3H), 2.95 (s, 3H), 2.64 (t, J = 7.6 Hz, 2H) ; 13 C-MR (125.8 MHz, CDCl 3 ) 171.2, 147.4, 132.2, 129.4, 119.1, 109.9, 37.1, 35.5, 34.3, 31.2; IR (KBr) 2918, , 1643 cm -1 ; HRMS (CI+) m/z calcd. for C 12 H 15 2 (M+H + ) , found METHD B,-Dimethyl-3-(pyridin-3-yl)propanamide (5a). 2 To a mixture of potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol), 3- chloropyridine (28.4 mg, 0.25 mmol), K 2 C 3 (103.7 mg, 0.75 mmol), Pd(Ac) 2 (1.4 mg, mmol) and SPhos (5.1 mg, mmol) under nitrogen was added toluene/h 2 (5:1, 1.2 ml). The reaction was heated at 85 ºC with stirring under a nitrogen atmosphere for 14 h and then cooled to rt. A solution of ph 7 buffer (4.0 ml) was added, and the resulting mixture was extracted with EtAc (3 3 ml). The organic layer was dried (MgS 4 ) and then filtered. The solvent was removed in vacuo and the crude product was purified by silica gel chromatography to afford the desired compound as a colorless oil in 50% yield (22.2 mg, mmol): 1 H-MR (500 MHz, CDCl 3 ) (m, 2H), 7.57 (d, J = 7.2 Hz, 1H), 7.22 (m, 1H), 2.99 (t, J = 7.5 Hz, 2H), 2.96 (br s, 6H), 2.63 (t, J = 7.6 Hz, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) 173.5, 151.9, 149.6, 138.9, 138.2, 125.4, 39.2, 37.5, 36.7, 30.4; IR (neat) 2932, 1637 cm -1 ; HRMS (CI+) m/z calcd. for C 10 H 15 2 (M+H + ) , found S5
6 CH 3-(4-Formylphenyl)-,-dimethylpropanamide (3b). This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and 4-chlorobenzaldehyde (35.1 mg, 0.25 mmol) according to Method A to afford the desired compound as a white solid in 87% yield (45.0 mg, 0.22 mmol): mp = ºC; 1 H-MR (500 MHz, CDCl 3 ) 9.97 (s, 1H), 7.81 (d, J = 7.9 Hz, 2H), 7.40 (d, J = 7.8 Hz, 2H), 3.06 (t, J = 7.7 Hz, 2H), 2.96 (s, 3H), 2.95 (s, 3H), 2.66 (t, J = 7.7 Hz, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) 192.0, 171.6, 149.1, 134.7, 130.1, 129.2, 37.2, 35.6, 34.5, 31.4; IR (KBr) 2931, 1700, 1643 cm -1 ; HRMS (CI+) m/z calcd. for C 12 H 16 2 (M+H + ) , found CMe 3-(4-Acetylphenyl)-,-dimethylpropanamide (3c). This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and 4-chloroacetophenone (38.7 mg, 0.25 mmol) according to Method A to afford the desired compound as a colorless oil in 94% yield (51.4 mg, 0.23 mmol): 1 H-MR (500 MHz, CDCl 3 ) 7.89 (d, J = 8.0 Hz, 2H), 7.32 (d, J = 8.0 Hz, 2H), 3.03 (t, J = 7.7 Hz, 2H), 2.95 (s, 6H), 2.64 (t, J = 7.7 Hz, 2H), 2.58 (s, 3H); 13 C-MR (125.8 MHz, CDCl 3 ) 197.8, 171.7, 147.4, 135.3, 128.7, 128.6, 37.2, 35.5, 34.6, 31.2, 26.6; IR (KBr) 2931, 1678, 1643 cm -1 ; HRMS (CI+) m/z calcd. for C 13 H 18 2 (M+H + ) , found CF 3 3-(4-(Trifluoromethyl)phenyl)-,-dimethylpropanamide (3d). S6
7 This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and 4-chlorobenzotrifluoride (45.1 mg, 0.25 mmol) according to Method A to afford the desired compound as a colorless oil in 76% yield (46.0 mg, 0.19 mmol): 1 H-MR (500 MHz, CDCl 3 ) 7.53 (d, J = 8.1 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 3.04 (t, J = 7.7 Hz, 2H), 2.95 (s, 6H), 2.63 (t, J = 7.8 Hz, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) 171.6, 145.8, 128.9, 128.6, (q), 37.2, 35.5, 34.7, 31.0; IR (neat) 2937, 1642 cm -1 ; HRMS (CI+) m/z calcd. for C 12 H 15 F 3 (M+H + ) , found ,-Dimethyl-3-(4-nitrophenyl)propanamide (3e). 3 This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and 4-chloronitrobenzene (39.4 mg, 0.25 mmol) according to Method A to afford the desired compound as a yellow oil in 85% yield (47.2 mg, 0.21 mmol): mp = ºC; 1 H-MR (500 MHz, CDCl 3 ) 8.14 (d, J = 8.5 Hz, 2H), 7.40 (d, J = 8.4 Hz, 2H), 3.09 (t, J = 7.5 Hz, 2H), 2.98 (s, 3H), 2.96 (s, 3H), 2.67 (t, J = 7.5 Hz, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) 171.2, 149.6, 146.5, 129.4, 123.7, 37.1, 35.5, 34.3, 30.9; IR (KBr) 2924, 1640, 1512, 1342 cm -1 ; HRMS (ES+) m/z calcd. for C 11 H (M+H + ) , found C 3-(2-Cyanophenyl)-,-dimethylpropanamide (3f). This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and 2-chlorobenzonitrile (34.4 mg, 0.25 mmol) according to Method A to afford the desired compound as a colorless oil in 83% yield (41.9 mg, 0.21 mmol): 1 H-MR (500 MHz, CDCl 3 ) 7.62 (d, J = 7.7 Hz, 1H), 7.52 (td, J = 7.7, 1.2 Hz, 1H), 7.44 (d, J = 7.6 Hz, 1H), 7.31 (t, J = 7.7 Hz, 1H), S7
8 3.19 (t, J = 7.7 Hz, 2H), 3.0 (s, 3H), 2.95 (s, 3H), 2.70 (t, J = 7.7 Hz, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) 171.1, 145.5, 133.0, 132.8, 130.2, 126.8, 118.1, 112.2, 37.2, 35.5, 34.1, 30.1; IR (neat) 2935, 2224, 1640 cm -1 ; HRMS (CI+) m/z calcd. for C 12 H 15 2 (M+H + ) , found C 2 Me Methyl 3-(2-(Dimethylcarbamoyl)ethyl)benzoate (3g). This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and methyl-3-chlorobenzoate (42.6 mg, 0.25 mmol) according to Method A to afford the desired compound as a colorless oil in 81% yield (47.7 mg, 0.20 mmol): 1 H-MR (500 MHz, CDCl 3 ) 7.90 (br s, 1H), 7.88 (dd, J = 7.7, 1.0 Hz, 1H), 7.44 (d, J = 7.6 Hz, 1H), 7.34 (t, J = 7.6 Hz, 1H), 3.91 (s, 3H), 3.02 (t, J = 7.8 Hz, 2H), 2.95 (s, 6H), 2.64 (t, J = 7.9 Hz, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) 171.8, 167.2, 141.8, 133.3, 130.3, 129.4, 128.5, 127.4, 52.1, 37.2, 35.4, 34.9, 31.0; IR (neat) 2951, 1720, 1644, 1287 cm -1 ; HRMS (CI+) m/z calcd. for C 13 H 18 3 (M+H + ) , found ,-Dimethyl-3-phenylpropanamide (4a). 4 This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and chlorobenzene (28.1 mg, 0.25 mmol) according to Method A to afford the desired compound as a colorless oil in 75% yield (33.3 mg, 0.19 mmol): 1 H-MR (500 MHz, CDCl 3 ) (m, 5H), 2.97 (t, J = 7.8 Hz, 2H), 2.95 (s, 3H), 2.92 (s, 3H), 2.61 (t, J = 7.9 Hz, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) 172.3, 141.6, , 128.5, 126.2, 37.2, 35.5, 35.4, 31.4; IR (neat) 2932, 1644 cm -1 ; HRMS (CI+) m/z calcd. for C 11 H 16 (M+H + ) , found S8
9 ,-Dimethyl-3-o-tolylpropanamide (4b). This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and 2-chlorotoluene (31.6 mg, 0.25 mmol) according to Method A to afford the desired compound as a colorless oil in 75% yield (35.8 mg, 0.19 mmol): 1 H-MR (500 MHz, CDCl 3 ) (m, 4H), (m, 2H), 2.95 (s, 3H), 2.94 (s, 3H), 2.55 (m, 2H), 2.33 (s, 3H); 13 C-MR (125.8 MHz, CDCl 3 ) 172.3, 139.6, 136.0, 130.3, 128.8, 126.3, 126.1, 37.2, 35.4, 33.9, 28.7, 19.3 IR (neat) 2935, 1643 cm -1 ; HRMS (CI+) m/z calcd. for C 12 H 18 (M+H + ) , found ,-Dimethyl-3-(2,6-dimethylphenyl)propanamide (4c). This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and 2-chloro-1,3-dimethylbenzene (35.2 mg, 0.25 mmol) according to Method A to afford the desired compound as a white solid in 76% yield (39.0 mg, 0.19 mmol): mp = ºC; 1 H-MR (500 MHz, CDCl 3 ) (m, 3H), 2.99 (m, 2H), 2.97 (s, 3H), 2.93 (s, 3H), 2.45 (m, 2H), 2.33 (s, 6H); 13 C-MR (125.8 MHz, CDCl 3 ) 172.4, 138.1, 136.3, 128.3, 126.1, 37.1, 35.5, 32.4, 25.2, 19.8; IR (KBr) 2962, 2923, 1639 cm -1 ; HRMS (ES+) m/z calcd. for C 13 H 19 a (M+a + ) , found Me Me 3-(3,5-Dimethoxyphenyl)-,-dimethylpropanamide (4d). S9
10 This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and 1-chloro-3,5-dimethoxybenzene (43.2 mg, 0.25 mmol) according to Method A to afford the desired compound as a colorless solid in 78% yield (46.1 mg, 0.19 mmol): mp = ºC; 1 H-MR (500 MHz, CDCl 3 ) 6.38 (m, 2H), 6.3 (m, 1H), 3.78 (s, 6H), 2.95 (s, 3H), 2.94 (s, 3H), 2.91 (t, J = 8.1 Hz, 2H), 2.60 (t, J = 8.0 Hz, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) 172.2, 160.9, 144.0, 106.5, 98.0, 55.3, 37.2, 35.5, 35.2, 31.7; IR (KBr) 2920, 2840, 1649, 1201, 1154 cm -1 ; HRMS (ES+) m/z calcd. for C 13 H 19 3 a (M+a + ) , found (4-(1H-Pyrrol-1-yl)phenyl)-,-dimethylpropanamide (4e). This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and 1-(4-chlorophenyl)-1H-pyrrole (44.4 mg, 0.25 mmol) according to Method A to afford the desired compound as a white solid in 89% yield (42.7 mg, 0.18 mmol): mp = ºC; 1 H-MR (500 MHz, CDCl 3 ) 7.30 (d, J = 8.6 Hz, 2H), 7.26 (d, J = 8.5 Hz, 2H), 7.04 (m, 2H), 6.32 (m, 2H), 2.99 (t, J = 7.7 Hz, 2H), 2.95 (s, 3H), 2.94 (s, 3H), 2.62 (t, J = 7.8 Hz, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) 171.9, 139.1, 139.0, 129.6, 120.6, 119.3, 110.2, 37.2, 35.5, 35.1, 30.7; IR (KBr) 2928, 1656, 1596, 1546 cm -1 ; HRMS (CI+) m/z calcd. for C 15 H 19 2 (M+H + ) , found Me 3-(4-Methoxyphenyl)-,-dimethylpropanamide (2a). 5 This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and 4-chloroanisole (35.6 mg, 0.25 mmol) according to Method A to afford the desired compound as a colorless oil in 86% yield (44.6 mg, 0.22 mmol): 1 H-MR (500 MHz, CDCl 3 ) 7.13 (d, S10
11 J = 8.5 Hz, 2H), 6.83 (d, J = 8.5 Hz, 2H), 3.78 (s, 3H), 2.94 (s, 3H), 2.92 (s, 3H), 2.91 (t, J = 7.9 Hz, 2H), 2.58 (t, J = 7.9 Hz, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) 172.3, 158.0, 133.5, 129.4, 113.9, 55.3, 37.2, 35.6, 35.4, 30.5; IR (neat) 2934, 1636, 1246 cm -1 ; HRMS (CI+) m/z calcd. for C 12 H 18 2 (M+H + ) , found F 3-(6-Fluoropyridin-3-yl)-,-dimethylpropanamide (5c). This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and 5-chloro-2-fluoropyridine (32.9 mg, 0.25 mmol) according to Method B to afford the desired compound as a colorless solid in 60% yield (29.3 mg, 0.15 mmol): mp = ºC; 1 H-MR (500 MHz, CDCl 3 ) 8.07 (br s, 1H), 7.69 (td, J = 8.1, 2.4 Hz, 1H), 6.85 (dd, J = 8.2, 2.7 Hz, 1H), 2.98 (t, J = 7.4 Hz, 2H), 2.97 (s, 3H), 2.95 (s, 3H), 2.62 (t, J = 7.4 Hz, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) 171.3, (d, J = Hz), (d, J = 17.3 Hz), (d, J = 7.6 Hz), (d, J = 4.6 Hz), (d, J = 37.2 Hz), 37.1, 35.5, 34.7, 27.3; IR (KBr) 2934, 2923, 1638, 1487 cm -1 ; HRMS (ES+) m/z calcd. for C 10 H 14 2 F (M+H + ) , found Me 3-(6-Methoxypyridin-3-yl)-,-dimethylpropanamide (5d). This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and 5-chloro-2-methoxypyridine (35.9 mg, 0.25 mmol) according to Method B to afford the desired compound as a colorless solid in 87% yield (45.1 mg, 0.22 mmol): mp = ºC; 1 H-MR (500 MHz, CDCl 3 ) 8.01 (s, 1H), 7.47 (dd, J = 8.5, 2.2 Hz, 1H), 6.67 (d, J = 8.4 Hz, 1H), 3.91 (s, 3H), 2.95 (br s, 6H), 2.90 (t, J = 7.6 Hz, 2H), 2.58 (t, J = 7.6 Hz, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) S11
12 171.7, 162.8, 146.1, 139.1, 129.4, 110.5, 53.3, 37.1, 35.4, 34.5, 27.4; IR (KBr) 2946, 1639, 1494 cm -1 ; HRMS (CI+) m/z calcd. for C 11 H (M+H + ) , found CH 3-(5-Formylfuran-2-yl)-,-dimethylpropanamide (5e). This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and 5-chloro-2-furaldehyde (32.6 mg, 0.25 mmol) according to Method B to afford the desired compound as a colorless solid in 73% yield (35.5 mg, 0.18 mmol): mp = ºC; 1 H-MR (500 MHz, CDCl 3 ) 9.52 (s, 1H), 7.18 (m, 1H), 6.32 (m, 1H), 3.10 (t, J = 7.4 Hz, 2H), 3.01 (s, 3H), 2.96 (s, 3H), 2.74 (t, J = 7.5 Hz, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) 177.0, 170.8, 162.7, 151.9, 109.5, 37.1, 35.5, 31.0, 24.0; IR (KBr) 2930, 1674, 1642 cm -1 ; HRMS (CI+) m/z calcd. for C 10 H 14 3 (M+H + ) , found S,-Dimethyl-3-(thiophen-2-yl)propanamide (5f). 2 This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and 2-chlorothiophene (29.6 mg, 0.25 mmol) according to Method B to afford the desired compound as a colorless oil in 79% yield (36.0 mg, 0.20 mmol): 1 H-MR (500 MHz, CDCl 3 ) 7.11 (dd, J = 5.1, 1.1 Hz, 1H), 6.91 (dd, J = 5.1, 3.4 Hz, 1H), 6.83 (m, 1H), 3.19 (m, 2H), 2.97 (s, 3H), 2.96 (s, 3H), 2.67 (m, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) 171.6, 144.2, 126.9, 124.7, 123.4, 37.2, 35.5, 35.5, 25.5; IR (neat) 2930, 1634 cm -1 ; HRMS (CI+) m/z calcd. for C 9 H 14 S (M+H + ) , found S12
13 S CH 3-(5-Formylthiophen-2-yl)-,-dimethylpropanamide (5g). This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and 5-chloro-2-thiophene carboxaldehyde (36.7 mg, 0.25 mmol) according to Method B to afford the desired compound as a colorless oil in 66% yield (35.0 mg, 0.17 mmol): 1 H-MR (500 MHz, CDCl 3 ) 9.82 (s, 1H), 7.62 (d, J = 3.7 Hz, 1H), 6.99 (d, J = 3.6 Hz, 1H), 3.23 (t, J = 7.3 Hz, 2H), 3.0 (s, 3H), 2.97 (s, 3H), 2.71 (t, J = 7.3 Hz, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) 182.7, 170.7, 156.1, 142.0, 137.1, 126.6, 37.1, 35.6, 34.5, 26.2; IR (neat) 2930, 1660, 1641 cm -1 ; HRMS (CI+) m/z calcd. for C 10 H 14 2 S (M+H + ) , found ,-Dimethyl-3-(2-methylquinolin-4-yl)propanamide (5h). This product was prepared from potassium -trifluoroborato-,-dimethylpropanamide (1a) (52.3 mg, mmol) and 4-chloro-2-methylquinoline (44.4 mg, 0.25 mmol) according to Method B to afford the desired compound as a colorless solid in 72% yield (43.5 mg, 0.18 mmol): mp = ºC; 1 H-MR (500 MHz, CDCl 3 ) 8.02 (d, J = 8.4 Hz, 1H), 8.01 (d, J = 8.4 Hz, 1H), 7.67 (dd, J = 8.2, 7.1 Hz, 1H), 7.50 (dd, J = 8.1, 7.1 Hz, 1H), 7.18 (s, 1H), 3.40 (m, 2H), 2.97 (s, 3H), 2.90 (s, 3H), 2.73 (m, 2H), 2.71 (s, 3H); 13 C-MR (125.8 MHz, CDCl 3 ) 171.5, 158.8, 148.1, 147.4, 129.5, 129.1, 125.7, 125.6, 123.2, 121.8, 37.1, 35.5, 33.5, 27.4, 25.3; IR (KBr) 2933, 1643 cm -1 ; HRMS (ES+) m/z calcd. for C 15 H 19 2 (M+H + ) , found Me 3-(2-Methoxyphenyl)-1-morpholinopropan-1-one (6a). S13
14 This product was prepared from potassium 3-trifluoroborato-1-morpholinopropan-1-one (2b) (62.9 mg, mmol) and 2-chloroanisole (35.6 mg, 0.25 mmol) according to Method A to afford the desired compound as a colorless oil in 65% yield (40.5 mg, 0.16 mmol): 1 H-MR (500 MHz, CDCl 3 ) (m, 2H), (m, 2H), 3.82 (s, 3H), (m, 4H), 3.50 (t, J = 4.7 Hz, 2H), 3.39 (t, J = 4.7 Hz, 2H), 2.94 (m, 2H), 2.58 (m, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) 171.6, 157.5, 130.3, 129.2, 127.7, 120.7, 110.3, 66.9, 66.6, 55.3, 46.0, 41.9, 33.2, 27.0; IR (neat) 2962, 2922, 2856, 1644, 1244, 1114 cm -1 ; HRMS (CI+) m/z calcd. for C 14 H 20 3 (M+H + ) , found Me 2-(2-Methoxybenzyl)-,-dimethylpropanamide (6b). This product was prepared from potassium 2-(trifluoroboratomethyl)-,-dimethylpropanamide (2c) (55.8 mg, mmol) and 2-chloroanisole (35.6 mg, 0.25 mmol) according to Method A to afford the desired compound as a colorless oil in 60% yield (33.5 mg, 0.15 mmol): 1 H-MR (500 MHz, CDCl 3 ) 7.20 (t, J = 7.8 Hz, 1H), 7.10 (d, J = 7.3 Hz, 1H), (m, 2H), 3.83 (s, 3H), 3.11 (m, 1H), 2.92 (dd, J = 13.0, 6.6 Hz, 1H), 2.90 (br s, 6H), 2.64 (dd, J = 13.0, 7.9 Hz, 1H), 1.08 (d, J = 6.7 Hz, 3H); 13 C- MR (125.8 MHz, CDCl 3 ) 176.5, 157.6, 131.4, 128.3, 127.6, 120.4, 110.1, 55.2, 36.9, 35.6, 35.5, 35.2, 17.1; IR (neat) 2963, 2932, 1641, 1243 cm -1 ; HRMS (CI+) m/z calcd. for C 13 H 20 2 (M+H + ) , found Ph H Me 3-(2-Methoxyphenyl)--phenylpropanamide (6c). This product was prepared from potassium 3-trifluoroborato--phenylpropanamide (2d) (64.4 mg, mmol) and 2-chloroanisole (35.6 mg, 0.25 mmol) according to Method A to afford the desired compound as a white solid in 84% yield (53.5 mg, 0.21 mmol): mp = ºC; 1 H-MR (500 MHz, S14
15 CDCl 3 ) 7.44 (m, 3H), (m, 4H), 7.05 (t, J = 7.3 Hz, 1H), (m, 2H), 3.79 (s, 3H), 3.02 (t, J = 7.6 Hz, 2H), 2.63 (t, J = 7.6 Hz, 2H); 13 C-MR (125.8 MHz, CDCl 3 ) 171.2, 157.4, 138.1, 130.2, , 128.9, 127.8, 124.2, 120.7, 120.0, 110.4, 55.3, 37.9, 25.6; IR (KBr) 2931, 1631, 1328 cm - 1 ; HRMS (CI+) m/z calcd. for C 16 H 18 2 (M+H + ) , found Corminboeuf,.; Renaud, P. rg. Lett. 2002, 4, Commercially available compound. 3 Russell, G. A.; Wang, K. J. rg. Chem. 1991, 56, Horiuchi, H.; Tsurugi, H.; Satoh, T.; Miura, M. J. rg. Chem. 2008, 73, Molander, G. A.; Petrillo, D. rg. Lett. 2008, 10, S15
16 BF 3 K 1a 1 H MR (500 MHz, DMS-d 6 ) spectrum of 1a (Table 1, entry 1) 13 C MR (125.8 MHz, DMS-d 6 ) spectrum of 1a (Table 1, entry 1) S16
17 BF 3 K 1a 19 F MR (470.8 MHz, DMS-d 6 ) spectrum of 1a (Table 1, entry 1) 11 B MR (128.4 MHz, DMS-d 6 ) spectrum of 1a (Table 1, entry 1) S17
18 1b BF 3 K 1 H MR (500 MHz, DMS-d 6 ) spectrum of 1b (Table 1, entry 2) 13 C MR (125.8 MHz, D 2 ) spectrum of 1b (Table 1, entry 2) S18
19 1b BF 3 K 19 F MR (470.8 MHz, D 2 ) spectrum of 1b (Table 1, entry 2) 11 B MR (128.4 MHz, D 2 ) spectrum of 1b (Table 1, entry 2) S19
20 BF 3 K 1c 1 H MR (500 MHz, DMS-d 6 ) spectrum of 1c (Table 1, entry 3) 13 C MR (125.8 MHz, DMS-d 6 ) spectrum of 1c (Table 1, entry 3) S20
21 BF 3 K 1c 19 F MR (470.8 MHz, DMS-d 6 ) spectrum of 1c (Table 1, entry 3) 11 B MR (128.4 MHz, DMS-d 6 ) spectrum of 1c (Table 1, entry 3) S21
22 Ph H 1d BF 3 K 1 H MR (500 MHz, DMS-d 6 ) spectrum of 1d (Table 1, entry 4) 13 C MR (125.8 MHz, DMS-d 6 ) spectrum of 1d (Table 1, entry 4) S22
23 Ph H 1d BF 3 K 19 F MR (470.8 MHz, DMS-d 6 ) spectrum of 1d (Table 1, entry 4) 11 B MR (128.4 MHz, DMS-d 6 ) spectrum of 1d (Table 1, entry 4) S23
24 Me BF 3 K 1e 1 H MR (500 MHz, D 2 ) spectrum of 1e (Table 1, entry 5) 13 C MR (125.8 MHz, DMS-d 6 ) spectrum of 1e (Table 1, entry 5) S24
25 Me BF 3 K 1e 19 F MR (470.8 MHz, D 2 ) spectrum of 1e (Table 1, entry 5) 11 B MR (128.4 MHz, D 2 ) spectrum of 1e (Table 1, entry 5) S25
26 H 2 1f BF 3 K 1 H MR (500 MHz, DMS-d 6 ) spectrum of 1f (Table 1, entry 6) 13 C MR (125.8 MHz, DMS-d 6 ) spectrum of 1f (Table 1, entry 6) S26
27 H 2 1f BF 3 K 19 F MR (470.8 MHz, DMS-d 6 ) spectrum of 1f (Table 1, entry 6) 11 B MR (128.4 MHz, DMS-d 6 ) spectrum of 1f (Table 1, entry 6) S27
28 2a Me 1 H MR (500 MHz, CDCl 3 ) spectrum of 2a (Table 3, entry 6) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 2a (Table 3, entry 6) S28
29 Me 2b 1 H MR (500 MHz, CDCl 3 ) spectrum of 2b (eq 2) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 2b (eq 2) S29
30 3a C 1 H MR (500 MHz, CDCl 3 ) spectrum of 3a (Table 2, entry 1) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 3a (Table 2, entry 1) S30
31 3b CH 1 H MR (500 MHz, CDCl 3 ) spectrum of 3b (Table 2, entry 2) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 3b (Table 2, entry 2) S31
32 3c CMe 1 H MR (500 MHz, CDCl 3 ) spectrum of 3c (Table 2, entry 3) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 3c (Table 2, entry 3) S32
33 3d CF 3 1 H MR (500 MHz, CDCl 3 ) spectrum of 3d (Table 2, entry 4) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 3d (Table 2, entry 4) S33
34 3e 2 1 H MR (500 MHz, CDCl 3 ) spectrum of 3e (Table 2, entry 5) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 3e (Table 2, entry 5) S34
35 C 3f 1 H MR (500 MHz, CDCl 3 ) spectrum of 3f (Table 2, entry 6) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 3f (Table 2, entry 6) S35
36 C 2 Me 3g 1 H MR (500 MHz, CDCl 3 ) spectrum of 3g (Table 2, entry 7) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 3g (Table 2, entry 7) S36
37 4a 1 H MR (500 MHz, CDCl 3 ) spectrum of 4a (Table 3, entry 1) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 4a (Table 3, entry 1) S37
38 4b 1 H MR (500 MHz, CDCl 3 ) spectrum of 4b (Table 3, entry 2) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 4b (Table 3, entry 2) S38
39 4c 1 H MR (500 MHz, CDCl 3 ) spectrum of 4c (Table 3, entry 3) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 4c (Table 3, entry 3) S39
40 Me 4d Me 1 H MR (500 MHz, CDCl 3 ) spectrum of 4d (Table 3, entry 4) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 4d (Table 3, entry 4) S40
41 4e 1 H MR (500 MHz, CDCl 3 ) spectrum of 4e (Table 3, entry 5) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 4e (Table 3, entry 5) S41
42 5a 1 H MR (500 MHz, CDCl 3 ) spectrum of 5a (Table 4, entry 1) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 5a (Table 4, entry 1) S42
43 5c F 1 H MR (500 MHz, CDCl 3 ) spectrum of 5c (Table 4, entry 3) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 5c (Table 4, entry 3) S43
44 5d Me 1 H MR (500 MHz, CDCl 3 ) spectrum of 5d (Table 4, entry 4) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 5d (Table 4, entry 4) S44
45 CH 5e 1 H MR (500 MHz, CDCl 3 ) spectrum of 5e (Table 4, entry 5) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 5e (Table 4, entry 5) S45
46 S 5f 1 H MR (500 MHz, CDCl 3 ) spectrum of 5f (Table 4, entry 6) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 5f (Table 4, entry 6) S46
47 S CH 5g 1 H MR (500 MHz, CDCl 3 ) spectrum of 5g (Table 4, entry 7) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 5g (Table 4, entry 7) S47
48 5h 1 H MR (500 MHz, CDCl 3 ) spectrum of 5h (Table 4, entry 8) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 5h (Table 4, entry 8) S48
49 Me 6a 1 H MR (500 MHz, CDCl 3 ) spectrum of 6a (Table 5, entry 2) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 6a (Table 5, entry 2) S49
50 Me 6b 1 H MR (500 MHz, CDCl 3 ) spectrum of 6b (Table 5, entry 3) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 6b (Table 5, entry 3) S50
51 Ph H Me 6c 1 H MR (500 MHz, CDCl 3 ) spectrum of 6c (Table 5, entry 4) 13 C MR (125.8 MHz, CDCl 3 ) spectrum of 6c (Table 5, entry 4) S51
Rameshwar Prasad Pandit and Yong Rok Lee * School of Chemical Engineering, Yeungnam University, Gyeongsan , Korea
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