Phosphine ligand triggered oxidative decarbonylative homocoupling of aromatic aldehydes: Selectively generating biaryls and diarylketones

Chemical Communications

Volumn 47, Issue 7, 2011, Pages 2161-2163

  Yang, Luo ^a   Zeng, Tieqiang ^a   Shuai, Qi ^a   Guo, Xiangyu ^a   Li, Chao Jun ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BIARYL DERIVATIVE; DIARYL KETONE; LIGAND; ORGANIC COMPOUND; PHOSPHINE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; OXIDATIVE DECARBONYLATIVE HOMOCOUPLING;

EID: 79551481537     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c0cc04921b     Document Type: Article

References (57)

1. J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev., 2002, 102, 1359
2. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem., Int. Ed., 2005, 44, 4442
3. S. P. Stanforth, Tetrahedron, 1998, 54, 263
4. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev., 2007, 107, 174
5. L.-C. Campeau, D. R. Stuart, K. Fagnou, Aldrichimica Acta, 2007, 40, 35
6. B. J. Li, S. D. Yang, Z. J. Shi, Synlett, 2008, 949
7. G. P. McGlacken, L. M. Bateman, Chem. Soc. Rev., 2009, 38, 2447
8. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res., 2009, 42, 1074
9. S. Yanagisawa, T. Sudo, R. Noyori, K. Itami, J. Am. Chem. Soc., 2006, 128, 11748
10. T. W. Lyons, M. S. Sanford, Chem. Rev., 2010, 110, 1147
11. R. Giri, B.-F. Shi, K. M. Engle, N. Maugel, J.-Q. Yu, Chem. Soc. Rev., 2009, 38, 3242
12. F. Pogan, P. H. Dixneuf, Adv. Synth. Catal., 2009, 351, 1737
13. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem., Int. Ed., 2009, 48, 9792
14. J. A. Ashenhurst, Chem. Soc. Rev., 2010, 39, 540
15. M. C. Kozlowski, B. J. Morgan, E. C. Linton, Chem. Soc. Rev., 2009, 38, 3193
16. J. Tsuji, Transition Metal Reagents and Catalysts, Wiley, New York, 2004
17. F. Diederich and P. J. Stang, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, Germany, 1998
18. M. Hudlicky, in Oxidations in Organic Chemistry, ACS Monograph 186, American Chemical Society, Washington, DC, 1990
19. R. C. Larock, Comprehensive Organic Transformations, VCH, New York, 1989, p. 591
20. G. Olah, Friedel-Crafts and Related Reactions, Interscience Publishers, New York, 1964, vol. III, p. 1259
21. M. Osman, Helv. Chim. Acta, 1982, 65, 2448
22. H. E. Zimmerman, D. H. Paskovich, J. Am. Chem. Soc., 1964, 86, 2149
23. F. R. Heitzler, H. Hopf, P. G. Jones, P. Bubenitschek, V. Lehne, J. Org. Chem., 1993, 58, 2781
24. A. Ianni, S. R. Waldvogel, Synthesis, 2006, 2103
25. R. K. Dieter, Tetrahedron, 1999, 55, 4177
26. T. Ishiyama, H. Kizaki, T. Hayashi, A. Suzuki, N. Miyaura, J. Org. Chem., 1998, 63, 4726
27. T. Ishiyama, H. Kizaki, N. Miyaura, A. Suzuki, Tetrahedron Lett., 1993, 34, 7595
28. R. C. Larock, Q. Tian, A. A. Pletnev, J. Am. Chem. Soc., 1999, 121, 3238
29. A. A. Pletnev, R. C. Larock, Tetrahedron Lett., 2002, 43, 2133
30. A. A. Pletnev, Q. Tian, R. C. Larock, J. Org. Chem., 2002, 67, 9276
31. C. Zhou, R. C. Larock, J. Am. Chem. Soc., 2004, 126, 2302
32. C. Zhou, R. C. Larock, J. Org. Chem., 2006, 71, 3551
33. H. Shimizu, M. Murakami, Chem. Commun., 2007, 2855
34. L. Zhao, X. Lu, Angew. Chem., Int. Ed., 2002, 41, 4343
35. T. Hirao, D. Misu, T. Agawa, J. Am. Chem. Soc., 1985, 107, 7179
36. T. Satoh, T. Itaya, M. Miura, M. Nomura, Chem. Lett., 1996, 823
37. T. Ishiyama, J. F. Hartwig, J. Am. Chem. Soc., 2000, 122, 12043
38. L. S. Liebeskind, J. Srogl, J. Am. Chem. Soc., 2000, 122, 11260
39. Y.-C. Huang, K. K. Majumdar, C.-H. Cheng, J. Org. Chem., 2002, 67, 1682
40. M. Pucheault, S. Darses, J.-P. Genet, J. Am. Chem. Soc., 2004, 126, 15356
41. M. C. Willis, Chem. Rev., 2010, 110, 725
42. C.-H. Jun, E.-A. Jo, J.-W. Park, Eur. J. Org. Chem., 2007, 1869
43. M. Garralda, Dalton Trans., 2009, 3635
44. P. J. Biju, G. S. R. S. Rao, Chem. Commun., 1999, 2225
45. C. M. Beck, S. E. Rathmill, Y. J. Park, J. Chen, R. H. Crabtree, Organometallics, 1999, 18, 5311
46. M. Kreis, A. Palmelund, L. Bunch, R. Madsen, Adv. Synth. Catal., 2006, 348, 2148
47. L. Yang, C. A. Correia, X. Guo, C.-J. Li, Tetrahedron Lett., 2010, 51, 5486
48. L. Yang, X. Guo, C.-J. Li, Adv. Synth. Catal., 2010, 352, 2899
49. X. Guo, J. Wang, C.-J. Li, J. Am. Chem. Soc., 2009, 131, 15092
50. X. Guo, J. Wang, C.-J. Li, Org. Lett., 2010, 12, 3176
51. J. Wang, X. Guo, C.-J. Li, J. Organomet. Chem., 2011, 696, 211
52. C. L. Allen, J. M. J. Williams, Angew. Chem., Int. Ed., 2010, 49, 1724
53. Q. Shuai, L. Yang, X. Guo, O. Basle, C.-J. Li, J. Am. Chem. Soc., 2010, 132, 12212
54. J. Tsuji, K. Ohno, Synthesis, 1969, 157
55. A. P. Kozikowski, H. F. Wetter, Synthesis, 1976, 561
56. Z. Shen, H. A. Khan, V. M. Dong, J. Am. Chem. Soc., 2008, 130, 2916
57. K. Tanaka, Y. Shibata, T. Suda, Y. Hagiwara, M. Hirano, Org. Lett., 2007, 9, 1215