Palladium-catalyzed direct α-arylation of methyl sulfones with aryl bromides

Organic Letters

Volumn 15, Issue 7, 2013, Pages 1690-1693

  Zheng, Bing ^a,b   Jia, Tiezheng ^b   Walsh, Patrick J ^b  

^a CHINA AGRICULTURAL UNIVERSITY   (China)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINATED HYDROCARBON; DIMETHYL SULFONE; DIMETHYL SULFOXIDE; PALLADIUM; SULFONE;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

CATALYSIS; DIMETHYL SULFOXIDE; HYDROCARBONS, BROMINATED; PALLADIUM; SULFONES;

EID: 84875964658     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400472v     Document Type: Article

References (44)

1. Andrei, G.; Naesens, L.; Snoeck, R.; Stephens, C. E. Patent: WO 2012/113920.
2. Caron, J. M. Patent: WO 2010/141956.
3. Chakravarty, P. K.; Shao, P. P. Patent: WO 2010/036596.
4. Harrak, Y.; Casula, G.; Basset, J.; Rosell, G.; Plescia, S.; Raffa, D.; Cusimano, M. G.; Pouplana, R.; Pujol, M. D. J. Med. Chem. 2010, 53, 6560
5. Sasikumar, T. K.; Qiang, L.; Burnett, D. A.; Cole, D.; Xu, R.; Li, H.; Greenlee, W. J.; Clader, J.; Zhang, L.; Hyde, L. Bioorg. Med. Chem. Lett. 2010, 20, 3632
6. Legros, L.; Dehli, J. R.; Bolm, C. Adv. Synth. Catal. 2005, 347, 19
7. Prinsep, M. R.; Blunt, J. W.; Munro, M. H. G. J. Nat. Prod. 1991, 54, 1068
8. Chou, S.-S. P.; Wu, C.-J. J. Tetrahedron 2012, 68, 5025
9. Chen, L.; Hua, Z.; Li, G.; Jin, Z. Org. Lett. 2011, 13, 3580
10. Cornes, D. Patent: WO 2002/100173.
11. Wichert, R. A.; Beckett, T. H. WO 2002/019823.
12. Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108
13. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382
14. Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1740
15. Culkin, D. A.; Hartwig, J. F. Acc. Chem. Rev. 2003, 36, 234
16. Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 1082
17. Johansson, C. C. C.; Colacot, T. J. Angew. Chem., Int. Ed. 2010, 49, 676
18. Novak, P.; Martín, R. Curr. Org. Chem. 2011, 15, 3233
19. Magano, J.; Dunetz, J. R. Chem. Rev. 2011, 111, 2177
20. Abd-El-Aziz, A. S.; De Denus, C. R. J. Chem. Soc., Perkin Trans. 1 1993, 293
21. Cho, G. Y.; Bolm, C. Org. Lett. 2005, 7, 1351
22. Gorelik, M. V.; Titova, S. P.; Kanor, M. A. Kano., Zh. Org. Khim. 1992, 28, 2294
23. Kim, S. H.; Lee, H. S.; Kim, K. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 6476
24. Makosza, M.-L.; Lemek, T.; Kwast, A.; Terrier, F. J. Org. Chem. 2002, 67, 394
25. Mitin, A. V.; Kashin, A. N.; Beletskaya, I. P. J. Organomet. Chem. 2004, 689, 1085
26. Sakamoto, T.; Katoh, E.; Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1990, 38, 1513
27. Suzuki, H.; Qui, Y.; Inoue, J.; Kusume, K.; Ogawa, T. Chem. Lett. 1987, 887
28. You, J.; Verkade, J. G. J. Org. Chem. 2003, 68, 8003
29. You, J.; Verkade, J. G. Angew. Chem., Int. Ed. 2003, 42, 5051
30. Kashin, A. N.; Mitin, A. V.; Beletskaya, I. P.; Wife, R. Tetrahedron Lett. 2002, 43, 2539
31. Renaud, P.; Bourquard, T.; Carrupt, P.-A.; Gerster, M. Helv. Chim. Acta 1998, 81, 1048
32. Niwa, T.; Yorimitsu, H.; Oshima, K. Tetrahedron 2009, 65, 1971
33. Zhou, G.; Ting, P. C.; Aslanian, R. G. Tetrahedron Lett. 2010, 51, 939
34. McGrew, G. I.; Temaismithi, J.; Carroll, P. J.; Walsh, P. J. Angew. Chem., Int. Ed. 2010, 49, 5541
35. Zhang, J.; Stanciu, C.; Wang, B.; Hussain, M. M.; Da, C.-S.; Carroll, P. J.; Dreher, S. D.; Walsh, P. J. J. Am. Chem. Soc. 2011, 133, 20552
36. McGrew, G. I.; Stanciu, C.; Zhang, J.; Carroll, P. J.; Dreher, S. D.; Walsh, P. J. Angew. Chem., Int. Ed. 2012, 51, 11510
37. Zhang, J.; Bellomo, A.; Creamer, A. D.; Dreher, S. D.; Walsh, P. J. J. Am. Chem. Soc. 2012, 134, 13765
38. Bellomo, A.; Zhang, J.; Trongsiriwat, N.; Walsh, P. J. Chem. Sci. 2013, 4, 849
39. Jia, T.; Bellomo, A.; Baina, K. E.; Dreher, S. D.; Walsh, P. J. J. Am. Chem. Soc. 2013, 135, 3740
40. Matthews, W. S.; Bares, J.; Bartmess, J. E.; Bordwell, F. G.; Cornforth, F. J.; Drucker, G. E.; Margolin, Z.; McCallum, R. J.; McCallum, G. J.; Vanier, N. R. J. Am. Chem. Soc. 1975, 97, 7006
41. Bordwell, F. G.; Branca, J. C.; Johnson, C. R.; Vanier, N. R. J. Org. Chem. 1980, 45, 3884
42. So, C. M.; Lau, C. P.; Kwong, F. Y. Org. Lett. 2007, 9, 2795
43. Lee, H. W.; Lam, F. L.; So, C. M.; Lau, C. P.; Chan, A. S. C.; Kwong, F. Y. Angew. Chem., Int. Ed. 2009, 48, 7436
44. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456