Pd(II)-catalyzed enantioselective C-H activation/C-O bond formation: Synthesis of chiral benzofuranones

Journal of the American Chemical Society

Volumn 135, Issue 4, 2013, Pages 1236-1239

  Cheng, Xiu Fen ^a   Li, Yan ^a   Su, Yi Ming ^a   Yin, Feng ^a   Wang, Jian Yong ^a   Sheng, Jie ^a   Vora, Harit U ^b   Wang, Xi Sheng ^a   Yu, Jin Quan ^b  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BOND FORMATION; C-H ACTIVATION; C-O BOND FORMATION; ENANTIOSELECTIVE; FUNCTIONALIZATIONS; PHENYLACETIC ACID; REDOX CATALYSIS;

ACTIVATION ANALYSIS; CATALYSIS; ENANTIOSELECTIVITY;

PALLADIUM COMPOUNDS;

3 BENZOFURANONE DERIVATIVE; PALLADIUM; PHENYLACETIC ACID;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHIRALITY; ENANTIOSELECTIVITY; OXIDATION REDUCTION REACTION; SYNTHESIS;

BENZOFURANS; CATALYSIS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 84873880768     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja311259x     Document Type: Article

References (70)

1. Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074
2. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
3. Xu, L.-M.; Li, B.-J.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712
4. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
5. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
6. Wencel-Delord, J.; Dröge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740-4761
7. Taber, D. F.; Stiriba, S.-E. Chem.-Eur. J. 1998, 4, 990
8. Godula, K.; Sames, D. Science 2006, 312, 67
9. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417
10. Ishihara, Y.; Baran, P. S. Synlett 2010, 1733
11. Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976
12. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885
13. Brückl, T.; Baxter, R. D.; Ishihara, Y.; Baran, P. S. Acc. Chem. Res. 2012, 45, 826
14. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
15. Wada, S.-I.; Hitomi, T.; Tokuda, H.; Tanaka, R. Chem. Biodivers. 2010, 7, 2303
16. Wada, S.-I.; Hitomi, T.; Tanaka, R. Helv. Chim. Acta 2009, 92, 1610
17. Shen, Z.; Falshaw, C. P.; Haslam, E.; Begley, M. J. J. Chem. Soc., Chem. Comm. 1985, 1135
18. Onan, K. D.; Kelley, C. J.; Patarapanich, C.; Leary, J. D.; Aladesanmi, A. J. J. Chem. Soc., Chem. Comm. 1985, 121
19. Ge, H. M.; Zhu, C. H.; Shi, D. H.; Zhang, L. D.; Xie, D. Q.; Yang, J.; Ng, S. W.; Tan, R. X. Chem.-Eur. J. 2008, 14, 376
20. Nicolaou, K. C.; Kang, Q.; Wu, T. R.; Lim, C. S.; Chen, D. Y.-K. J. Am. Chem. Soc. 2010, 132, 7540
21. Nicolaou, K. C.; Wu, T. R.; Kang, Q.; Chen, D. Y.-K. Angew. Chem., Int. Ed. 2009, 48, 3440
22. Engle, K. M.; Mei, T.-S.; Wang, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2011, 50, 1478
23. Jordan-Hore, J. A.; Johansson, C. C. C.; Gulias, M.; Beck, E. M.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 16184
24. Mei, T.-S.; Wang, X.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 10806
25. Wang, X.; Lu, Y.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 12203
26. Wei, Y.; Yoshikai, N. Org. Lett. 2011, 13, 5504
27. Zhang, S.-Y.; He, G.; Zhao, Y.; Wright, K.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2012, 134, 7313
28. Huntress, E. H.; Hearon, W. M. J. Am. Chem. Soc. 1941, 63, 2762
29. Shankaran, K.; Sloan, C. P.; Snieckus, V. Tetrahedron Lett. 1985, 26, 6001
30. Motallebi, S.; Müller, P. Helv. Chim. Acta 1993, 76, 2803
31. Anacardio, R.; Arcadi, A.; DAnniballe, G.; Marinelli, F. Synthesis 1995, 831
32. Satoh, T.; Tsuda, T.; Kushino, Y.; Miura, M.; Nomura, M. J. Org. Chem. 1996, 61, 6476
33. Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413
34. Ye, F.; Alper, H. Adv. Synth. Catal. 2006, 348, 1855
35. Huang, C.; Chattopadhyay, B.; Gevorgyan, V. J. Am. Chem. Soc. 2011, 133, 12406
36. Molander, G. A.; Cavalcanti, L. N. J. Org. Chem. 2011, 76, 623
37. Zhu, C.; Wang, R.; Falck, J. R. Org. Lett. 2012, 14, 3494
38. Covell, D. J.; White, M. C. Angew. Chem., Int. Ed. 2008, 47, 6448
39. Takenaka, K.; Akita, M.; Tanigaki, Y.; Takizawa, S.; Sasai, H. Org. Lett. 2011, 13, 3506
40. Novák, P.; Correa, A.; Gallardo-Donaire, J.; Martin, R. Angew. Chem., Int. Ed. 2011, 50, 12236
41. Pd-catalyzed hydroxyl-directed C-H activation/C-O bond formation: Xiao, B.; Gong, T.-J.; Liu, Z.-J.; Liu, J.-H.; Luo, D.-F.; Xu, J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 9250 See also refs 4e,4f
42. Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882
43. Shi, B.-F.; Zhang, Y.-H.; Lam, J. K.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 460
44. Wasa, M.; Engle, K. M.; Lin, D. W.; Yoo, E. J.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 19598
45. Albicker, M. R.; Cramer, N. Angew. Chem., Int. Ed. 2009, 48, 9139
46. Renaudat, A.; Jean-Gérard, L.; Jazzar, R.; Kefalidis, C. E.; Clot, E.; Baudoin, O. Angew. Chem., Int. Ed. 2010, 49, 7261
47. Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Angew. Chem., Int. Ed. 2011, 50, 7438
48. Anas, S.; Cordi, A.; Kagan, H. B. Chem. Commun. 2011, 47, 11483
49. Shintani, R.; Otomo, H.; Ota, K.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 7305
50. Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765
51. García-Urdiales, E.; Alfonso, I.; Gotor, V. Chem. Rev. 2005, 105, 313
52. Studer, A.; Schleth, F. Synlett 2005, 3033
53. Rovis, T. In New Frontiers in Asymmetric Catalysis; Mikami, K.; Lautens, M., Eds.; John Wiley & Sons, Inc.: New York, 2007; pp 275-309.
54. Atodiresei, I.; Schiffers, I.; Bolm, C. Chem. Rev. 2007, 107, 5683
55. Zhou, F.; Guo, J.; Liu, J.; Ding, K.; Yu, S.; Cai, Q. J. Am. Chem. Soc. 2012, 134, 14326
56. Grigg, R.; Putnikovic, B.; Urch, C. J. Tetrahedron Lett. 1996, 37, 695
57. Hills, I. D.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 3921
58. Shaw, S. A.; Aleman, P.; Vedejs, E. J. Am. Chem. Soc. 2003, 125, 13368
59. Trost, B. M.; Cramer, N.; Silverman, S. M. J. Am. Chem. Soc. 2007, 129, 12396
60. Li, X.; Hu, S.; Xi, Z.; Zhang, L.; Luo, S.; Cheng, J.-P. J. Org. Chem. 2010, 75, 8697
61. Zhu, C.-L.; Zhang, F.-G.; Meng, W.; Nie, J.; Cahard, D.; Ma, J.-A. Angew. Chem., Int. Ed. 2011, 50, 5869
62. Cao, Y.; Jiang, X.; Liu, L.; Shen, F.; Zhang, F.; Wang, R. Angew. Chem., Int. Ed. 2011, 50, 9124
63. Cassani, C.; Tian, X.; Escudero-Adán, E. C.; Melchiorre, P. Chem. Commun. 2011, 47, 233
64. Yoneyama, T.; Crabtree, R. H. J. Mol. Catal. A: Chem. 1996, 108, 35
65. Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300
66. Muñiz, K. Angew. Chem., Int. Ed. 2009, 48, 9412
67. Hickman, A. J.; Sanford, M. S. Nature 2012, 484, 177 See also refs 1d,1e.
68. Amino acid ligand-accelerated C-H functionalization: Wang, D.-H.; Engle, K. M.; Shi, B.-F.; Yu, J.-Q. Science 2010, 327, 315
69. Huang, C.; Ghavtadze, N.; Chattopadhyay, B.; Gevorgyan, V. J. Am. Chem. Soc. 2011, 133, 17630
70. Huang, C.; Ghavtadze, N.; Godoi, B.; Gevorgyan, V. Chem.-Eur. J. 2012, 18, 9789