Supporting Information. Pd(0)-Catalyzed Decarboxylative Coupling and Tandem C H Arylation/Decarboxylation for the. Synthesis of Heteroaromatic Biaryls
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1 Supporting Information Pd()-Catalyzed Decarboxylative Coupling and Tandem C H Arylation/Decarboxylation for the Synthesis of Heteroaromatic Biaryls Debkumar andi, Yang-Ming Jhou, Jhen-Yi Lee, Bing-Chiuan Kuo, Chien-Yu Liu, Pei-Wen Huang and Hon Man Lee* Department of Chemistry, ational Changhua University of Education, Changhua 558, Taiwan, R..C. leehm@cc.ncue.edu.tw Table of Content 1. Details of X-ray Diffraction Studies S2 2. Crystallographic Data for 1, 6, 17A, 17B, 21A and 23A S3 S4 3. Catalytic Table S4 4. X-ray Structures for 1, 6, 17A, 17B, 21A and 23A S5 S7 5. Proposed Catalytic Cycles S8 6. Copies of MR spectra S9 S27 S1
2 X-Ray Diffraction Studies. Compound 1 was collected at 1(2) K on with a CCD area detector. Graphite-monochromatized Mo Kα radiation was used (λ =.7173 Å). Data collection and reduction were performed using CrysAlisPro software. 1 Single-crystal X-ray diffraction data for all others were collected with a CCD area detector and a graphite monochromater utilizing Mo Kα radiation (λ =.7173 Å) at 15(2) K. The unit cell parameters were obtained by least-squares refinement. The data were integrated via SAIT. 2 Lorentz and polarization effect and multiscan absorption corrections were applied with SADABS. 3 The structures were solved by direct methods and refined by full-matrix least squares methods against F 2 with SHELXTL. 4 All non-h atoms were refined anisotropically. All H-atoms were fixed at calculated positions and refined with the use of a riding model. CCDC (1), (6), (17A), (17B), (21A), and (23A) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via S2
3 Table S1. Crystallographic Data empirical formula 1 C 4 H 8.5C 6 H A 17B 21A 23A C 46 H Pd C 15 H 12 2 C 16 H 12 2 C 16 H 12 2 C 19 H 15 C 16 H 15 C 4 H 8.5C 6 H 14 formula weight crystal system monoclinic triclinic monoclinic orthorhombic monoclinic orthorhombic space group P2 1 /n Pī P2 1 /n P P2 1 /c P a, Å (3) (2) (2) 7.94(3) (2) 7.243(15) b, Å (4) (2) 17.51(4) (4) (4) 9.93(2) c, Å (3) (2) (2) (8) 7.464(1) (4) α, deg (1) β, deg (2) (1) (1) (1) 9 γ, deg (1) V, Å (16) 563.9(2) (5) (9) (4) (5) T, K 1(2) 15(2) 15(2) 15(2) 15(2) 15(2) D, g/cm Z no. of unique data no. of params refined R 1 a [I > 2σI] wr 2 b (all data) a R 1 = Σ( F o F c )/Σ F o. b wr 2 = [Σ( F o 2 F c 2 ) 2 /Σ (F o 2 )] 1/2 S3
4 Table S2. Selected bond distances (Å) and Angles ( ) of 1 1 Pd1 C1 2.52(4) Pd1 C (3) Pd1 C (4) Pd1 C (4) C1 Pd1 C (13) C1 Pd1 C (15) C23 Pd1 C (14) C24 Pd1 C (15) C1 Pd1 C (14) C23 Pd1 C (15) Table S3. Tandem C H arylation and decarboxylation of 1-methylindole-3-carboxylic acid and aryl halides mediated by different catalyst systems a entry cat. yield (%) c 15A:15C b 6 3:1 3 Pd(Ac) 2/2L HCl Pd(Ac) 2/2PCy :1 5 Pd(PPh 3) a Reaction conditions: 3. mmol 2', 3. mmol 4-bromoacetophenone, 6. mmol KAc, 4 ml dry DMA, 2.5 mol % 1, 16 ºC, isolated yield, 24 h, L HCl = ligand precursor in 1. b 3 equiv. 4-bromoacetophenone. c isolate yield. S4
5 Figure S1. Molecular structure of 1 (5% probability level) Figure S2. Molecular structure of 6 (5% probability level) S5
6 Figure S3. Molecular structure of 17A (5% probability level) Figure S4. Molecular structure of 17B (5% probability level) S6
7 Figure S5. Molecular structure of 21A (5% probability level) Figure S6. Molecular structure of 23A (5% probability level) S7
8 Me F PdL 2 Me CH F Me PdLH Me CPdLH F F Scheme S1. A proposed catalytic cycle for the decarboxylation mediated by 1 Scheme S2. A proposed catalytic cycle for the decarboxylation coupling mediated by 1 S8
9 MESITYL CH3 LIGAD PRECURSR H.ESP ormalized Intensity Cl Figure S7. 1 H MR spectrum of [LH] + Cl - 1. MESITYL CH3 LIGAD PRECURSR C13.ESP Cl ormalized Intensity Figure S8. 13 C{ 1 H} MR spectrum of [LH] + Cl - S9
10 MESITYL PD() CH3 CMPLEX H.ESP R R ormalized Intensity Pd R = mesityl Figure S9. 1 H MR spectrum of 1 MESITYL PD() CH3 CMPLEX C ESP R R.5 ormalized Intensity Pd R = mesityl Figure S1. 13 C{ 1 H} MR spectrum of 1 S1
11 1. complex 2.esp ormalized Intensity Figure S11. 1 H MR spectrum of 2 1. complex 3.esp F.8.7 ormalized Intensity Figure S12. 1 H MR spectrum of 3 S11
12 complex 4.ESP ormalized Intensity Figure S13. 1 H MR spectrum of 4 1. complex 5.esp ormalized Intensity Figure S14. 1 H MR spectrum of 5 S12
13 1. complex 6.esp ormalized Intensity Figure S15. 1 H MR spectrum of 6 complex 7.esp ormalized Intensity Figure S16. 1 H MR spectrum of 7 S13
14 1. complex 8.esp ormalized Intensity Figure S17. 1 H MR spectrum of 8 1. complex 9.esp ormalized Intensity Figure S18. 1 H MR spectrum of 9 S14
15 complex 1.esp CH 3.7 ormalized Intensity Figure S19. 1 H MR spectrum of 1 1. complex 11.esp F.7 ormalized Intensity Figure S2. 1 H MR spectrum of 11 S15
16 1. complex 11-C13.esp.9.8 F.7 ormalized Intensity Figure S C{ 1 H} MR spectrum of 11 complex 12.esp F.8.7 ormalized Intensity Figure S22. 1 H MR spectrum of 12 S16
17 1. complex 12-C13.esp F ormalized Intensity Figure S C{ 1 H} MR spectrum of complex 13.esp.9.8 H 3 C.7 ormalized Intensity F Figure S24. 1 H MR spectrum of 13 S17
18 .8 complex 13-C13.esp.7 H 3 C.6 ormalized Intensity F Figure S C{ 1 H} MR spectrum of complex 14.esp F.8.7 ormalized Intensity Figure S26. 1 H MR spectrum of 14 S18
19 1. complex 15A.esp ormalized Intensity Figure S27. 1 H MR spectrum of 15A complex 15B.esp ormalized Intensity Figure S28. 1 H MR spectrum of 15B S19
20 1. complex 15C.esp ormalized Intensity Figure S29. 1 H MR spectrum of 15C complex 15c-C13.esp ormalized Intensity Figure S3. 13 C{ 1 H} MR spectrum of 15C S2
21 complex 16.esp ormalized Intensity Figure S31. 1 H MR spectrum of 16A complex 16A-C13.esp.3.25 ormalized Intensity Figure S C{ 1 H} MR spectrum of 16A S21
22 complex 17A.esp ormalized Intensity Figure S33. 1 H MR spectrum of 17A complex 17B.esp ormalized Intensity Figure S34. 1 H MR spectrum of 17B S22
23 1. complex 17B-C13.esp ormalized Intensity Figure S C{ 1 H} MR spectrum of 17B 1. complex 18A.esp ormalized Intensity Figure S36. 1 H MR spectrum of 18A S23
24 .8 complex 18A-C13.esp.7.6 ormalized Intensity Figure S C{ 1 H} MR spectrum of 18A complex 19.esp ormalized Intensity Figure S38. 1 H MR spectrum of 19A S24
25 complex 2.esp Water H 3 C.8 CH 3 ormalized Intensity H 3 C Figure S39. 1 H MR spectrum of 2A 1. comokex 2A-C13.esp.9.8 H 3 C ormalized Intensity H 3 C CH Figure S4. 13 C{ 1 H} MR spectrum of 2A S25
26 1. complex 21A.esp ormalized Intensity Figure S41. 1 H MR spectrum of 21A complex 22.esp ormalized Intensity H 3 C Figure S42. 1 H MR spectrum of 22A S26
27 complex 23A.esp ormalized Intensity Figure S43. 1 H MR spectrum of 23A References 1. CrysAlisPro. xford Diffraction Ltd., Abingdon, England, R. A. Hughes and C. J. Moody, Angew. Chem. Int. Ed., 27, 46, G. M. Sheldrick, SADABS. University of Göttingen, Germany, G. Sheldrick, Acta Crystallogr., 28, A64, S27
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