Pt IV azido complexes undergo copper-free click reactions with alkynes
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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 208 Pt IV azido complexes undergo copper-free click reactions with alkynes Electronic Supplementary Information icola J. Farrer, a* Gitanjali Sharma, a Rachel Sayers, a Evyenia Shaili, b Peter J. Sadler b Synthesis and Characterisation Mono-substituted trans-[pt(c 6 H )( 3 )(py) 2 ] Dimethyl acetylenedicarboxylate (2, 30.9 μl, 0.25 mmol) in MeH (5 ml) was added dropwise to trans-[pt( 3 ) 2 (py) 2 ] (00 mg, 0.23 mmol) in MeH (50 ml). The solution was stirred at 35 C for 2 days and then reduced to dryness. The solution was resuspended in minimal MeC, filtered (IM) and purified by HPLC under neutral conditions to give the monosubstituted complex as a pale yellow solid (43 mg, 0.07 mmol, 32 %). H MR (400 MHz, d 3 -MeC) δ: 8.73 (d, 4H, 3 J HH = 7, 3 J HPt = 38, H o ), 7.97 (dd, 2H, 3 J HH = 7, H p ), 7.49 (dd, 3 J HH = 7, H m ), 3.76 (s, Me, 6H). 95 Pt MR (86 MHz, d 3 -MeC) δ: (W ½ 50 Hz). ESI-MS (MeH) (M = trans-[pt(c 6 H )( 3 )(py) 2 ]) m/z: 602. ([M + a] +, calcd ); ([M + H] + calcd ) HRMS (MeH) m/z: ([M + H] +, C₁₆H₁₇₈₄Pt, calcd ). IR v cm - : 2043 ( 3 ), 728, 452, 289, 72, 090, 769, 693. Bis-substituted trans-[pt(c 6 H ) 2 (py) 2 ] Dimethyl acetylenedicarboxylate (2, 4 μl,.4 mmol) and trans-[pt( 3 ) 2 (py) 2 ] (00 mg, mmol) were stirred in MeH (50 ml) at 35 C for 3 d before the solvent was reduced in volume to 2 ml and placed in the fridge overnight. The solution was filtered and the precipitate washed with cold MeH to give the title compound as a white solid (7.5 mg, 0.03 mmol, %). MR spectroscopic experiments were run on freshly made solutions since the complex was unstable in d 6 -acetone. H MR (600 MHz, d 6 -acetone) δ: 8.67 (d, 4H, 3 J HH = 6, H o ), 8.03 (dd, 2H, 3 J HH = 7, H p ), 7.55 (dd, 3 J HH = 7, H m ), 3.90 (6H, Me), 3.75 (6H, Me). 4 MR (43 MHz, d 6 - acetone) δ: (sharp, 2 gas), 26. (br, W /2 909 Hz triazole ), 75.4 (br, W /2 793 Hz, py / triazole ). 95 Pt MR (29 MHz, d 6 -acetone) δ: -233 (W /2 00 Hz). ESI-MS (MeH) m/z: (M = trans-[pt(c 6 H ) 2 (py) 2 ]): ([2M + a] + calcd ); ([2M + H] + calcd ); ([M + a] + calcd 744.0);
2 ([M + H] + calcd ). HRMS (MeH) m/z: ([M + a] +, C₂₂H₂₂₈₈Pta, calcd ). IR ν cm - : 726, 454, 209, 72, 77, 693. Rearrangement complex 2a DMAD (2, 4 μl, 0.7 mmol) in MeH (2 ml) was added dropwise to (50 mg, 0.06 mmol) in MeH (3 ml). The solution was stirred at 35 C for 7d before being placed on ice. Product 2a was isolated as a white precipitate by filtration and rinsed with cold H 2, MeH and diethylether (8 mg, 0.03 mmol, 28 %). Complex 2a could also be obtained by dissolving 2a in CDCl 3 and leaving for several days. H MR (500 MHz, CDCl 3 ) δ: 9.0 (d, 3 J HPt = 27, 3 J HH = 6.0, 4H, H o ), 8.08 (t, 3 J HH = 6, J HH = 6, 2H, H p ), 7.66 (dd, 3 J HH = 6, 3 J HH = 6, 4H, H m ), 3.88 (s, CH 3, 3H), 2.89 (br, H),.69 (br, H). 95 Pt MR (07 MHz, CDCl 3 ) δ: 764 (PWHH 680 ppm). 4 MR (29 MHz, CDCl 3 ) δ: ( 2 gas), ( β ), 68.2 ( γ / py ). α not seen. 3 C MR (25 MHz, CDCl 3 ) δ: 64.3 (ester), 60.8 (ester), 49.4 C pyortho ), 42.2 (C pypara ), 39. ( 3 J CPt= 3.0, C triazole ), 35.6 ( 3 J CPt = 8.0, C triazole ), 27. ( 3 J CPt = 27.0, C pymeta ), 52.4 (C alkyl ). IR (solid) ν cm - : 3465, 2048 ( asym 3 ), 733, 675, 6, 483, 437, 389, 338, 265, 255, 222, 2, 28, 090, 079, 836, 774, 69. ESI-MS identical to 2a. Rearrangement complex 2b Complex 2b was obtained by dissolving 2b in CDCl 3 and leaving for several days. H MR (400 MHz, CDCl 3 ) δ: 8.94 (d, 3 J HPt = 27.0, 3 J HH = 6, 2H, H o ), 8.84 (dd, 3 J HPt = 27.0, 3 J HH = 6, 2H, H o ), 8.0 (t, 3 J HH = 6, H, H p ), 8.08 (t, 3 J HH = 6, H, H p ), 7.63 (m, 3 J HH = 6, 4H, H m ), 3.9 (s, CH 3, 3H), 3.88 (s, CH 3, 3H). 2
3 a) 2 β γ py α b) 2 Figure S. 4 MR (43 MHz) (d 6 -acetone) spectra of a) trans-[pt( 3 ) 2 (py) 2 ] starting material and b) bis substituted trans-[pt(c 6 H ) 2 (py) 2 ]. 3
4 a) 2 β γ/py α b) 2 c) Figure S2. 4 MR spectra of a) complex (D 2, 43 MHz) starting material b) complex 2a (D 2, 29 MHz) and c) complex 2a (CDCl 3, 28 MHz). 4
5 a) b) Figure S3. Solid-state IR spectra of a) mono-substituted 2a and b) bis-substituted 2b. 5
6 % py, [Pt(H)(C 6 H )(py)] m/z H Me Me H 2-84, Me 2 C C 2 Me H Pt H Me 2 C + H C 2 Me Figure S4. MS/MS of 2b: bis-substituted DMAD complex trans,trans,trans-[pt (C 6 H ) 2 (H) 2 (py) 2 + H] +, m/z (model m/z). % [Pt(H)(C 6 H )(py)] py C 5 H H - CH 3 H Me 2 C C 2 Me H Pt +H C 2 Me [Pt(H)(py) 2 ] Figure S5. MS/MS of species intermediate between 2b and 2b : bis-substituted, mono-axially tethered DMAD complex trans,trans,trans- [Pt(C 6 H ) 2 (C 5 H )(H)(py) 2 + H] +, 724. m/z (model m/z). 6
7 F-B4-68A H H + a + a 3 Pt Pt 3 CD 3 % m/z m/z m/z Figure S6. ESI-MS (MeC) of crystalline DEACD product 3a from reaction in d 4 - MeH: a mixture of cyclometallated transesterified species [Pt(py) 2 ( 3 )(H)( 3 C 5 4 D 3 ) + a] + at m/z (model m/z) and cyclometallated product [Pt(py) 2 ( 3 )(H)(C 6 H ) +a] + at m/z (model m/z). 7
8 UV-vis spectra a) 2.5 Absorbance (normalised) 2.5 2a 2a' 2b' Wavelength/nm b) 8
9 c) 2 Absorbance (normalised) a 2b Wavelength/nm Figure S7. UV-Vis spectra of and its derivatives in MeC/H 2, with absorbance normalised at 2 nm for all species: a) DMAD (2) derivatives b) BC () derivatives c) DBC (2) derivatives 9
10 0
11 Figure S8. HRMS of DBC products 2a ( m/z, top) and 2b ( m/z, bottom) with isotope predictions. References. J. Farrer, P. Gierth and P. J. Sadler, Chem. Eur. J., 20, 7,
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