Role of sterically demanding chiral dirhodium catalysts in site-selective C-H functionalization of activated primary C-H bonds

Journal of the American Chemical Society

Volumn 136, Issue 27, 2014, Pages 9792-9796

  Qin, Changming ^a   Davies, Huw M L ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EXCITONS; RHODIUM;

C-H FUNCTIONALIZATION; C-H INSERTION; DIRHODIUM; ELECTRONIC EFFECTS; ENANTIOSELECTIVE; SITE SELECTIVE; SITE SELECTIVITY; STERICALLY DEMANDING;

CATALYST SELECTIVITY;

ACETIC ACID DERIVATIVE; ALLYL COMPOUND; BENZILIC ACID; CARBENE; CARBOXYLIC ACID DERIVATIVE; RHODIUM; RHODIUM DERIVATIVE; STEROID;

ARTICLE; CATALYST; CHIRALITY; CYCLOPROPANATION; DIASTEREOISOMER; ELECTRONICS; ENANTIOSELECTIVITY; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 84904012650     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja504797x     Document Type: Article

References (44)

1. Godula, K.; Sames, D. Science 2006, 312, 67
2. McMurray, L.; OHara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885
3. Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976
4. Egger, J.; Carreira, E. M. Nat. Prod. Rep. 2014, 31, 449
5. Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2180
6. Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633
7. Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507
8. Handbook of C-H Transformations: Applications in Organic Synthesis; Dyker, G., Ed.; Wiley-VCH: Weinheim, Germany, 2005.
9. Bergman, R. G. Nature 2007, 446, 391
10. Hartwig, J. Organotransition Metal Chemistry: From Bonding to Catalysis; University Science Books: Sausalito, CA, 2010.
11. C-H Activation; Yu, J.-Q.; Shi, Z., Eds.; Topics in Current Chemistry, Vol. 292; Springer: Berlin, 2010.
12. Ferreira, E. M. Nat. Chem. 2014, 6, 94
13. Li, B.; Yang, S. D.; Shi, Z. J. Synlett 2008, 949
14. Engle, K. M.; Mei, T. S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788
15. Neufeldt, S. R.; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936
16. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814
17. Thu, H. Y.; Tong, G. S. M.; Huang, J. S.; Chan, S. L. F.; Deng, Q. H.; Che, C. M. Angew. Chem., Int. Ed. 2008, 47, 9747
18. Zalatan, D. N.; Du Bois, J. Top. Curr. Chem. 2010, 292, 347
19. Lu, H. J.; Zhang, X. P. Chem. Soc. Rev. 2011, 40, 1899
20. Hartwig, J. F. Acc. Chem. Res. 2012, 45, 864
21. White, M. C. Science 2012, 335, 807
22. Hashiguchi, B. G.; Bischof, S. M.; Konnick, M. M.; Periana, R. A. Acc. Chem. Res. 2012, 45, 814
23. Pan, S. C. Beilstein J. Org. Chem. 2012, 8, 1374
24. Brustad, E. M. Nat. Chem. Biol. 2014, 10, 170
25. Gorminsky, P. E.; White, M. C. J. Am. Chem. Soc. 2013, 135, 14052
26. Davies, H. M. L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857
27. Davies, H. M. L.; Lian, Y. Acc. Chem. Res. 2012, 45, 923
28. Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssié, P. Bull. Soc. Chim. Belg. 1984, 93, 945
29. Davies, H. M. L.; Hansen, J. J. Am. Chem. Soc. 1997, 119, 9075
30. Davies, H. M. L.; Hansen, T.; Churchill, M. R. J. Am. Chem. Soc. 2000, 122, 3063
31. Doyle, M. P.; Hu, W. J. Org. Chem. 2000, 65, 8839
32. Muller, P.; Tohill, S. Tetrahedron 2000, 56, 1725
33. Davies, H. M. L.; Coleman, M. G.; Ventura, D. L. Org. Lett. 2007, 9, 4971
34. Ventura, D. L.; Li, Z.; Coleman, M. G.; Davies, H. M. L. Tetrahedron 2009, 65, 3052
35. Nadeau, E.; Li, Z.; Morton, D.; Davies, H. M. L. Synlett 2009, 151
36. Davies, H. M. L.; Jin, Q.; Ren, P.; Kovalevsky, A. Y. J. Org. Chem. 2002, 67, 4165
37. Davies, H. M. L.; Jin, Q. Tetrahedron: Asymmetry 2003, 14, 941
38. Davies, H. M. L.; Jin, Q. Org. Lett. 2004, 6, 1769
39. Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. F. J. Am. Chem. Soc. 1996, 118, 6897
40. Davies, H. M. L.; Panaro, S. A. Tetrahedron Lett. 1999, 40, 5287
41. Reddy, R. P.; Lee, G. H.; Davies, H. M. L. Org. Lett. 2006, 8, 3437
42. Qin, C.; Boyarskikh, V.; Hansen, J. H.; Hardcastle, K. I.; Musaev, D. G.; Davies, H. M. L. J. Am. Chem. Soc. 2011, 133, 19198
43. Qin, C.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 14516
44. Qin, C.; Davies, H. M. L. Org. Lett. 2013, 15, 310