Retention or inversion in stereospecific nickel-catalyzed cross-coupling of benzylic carbamates with arylboronic esters: Control of absolute stereochemistry with an achiral catalyst

Journal of the American Chemical Society

Volumn 135, Issue 9, 2013, Pages 3303-3306

  Harris, Michael R ^a   Hanna, Luke E ^a   Greene, Margaret A ^a   Moore, Curtis E ^b   Jarvo, Elizabeth R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE STEREOCHEMISTRY; ACHIRAL CATALYST; BENZYLIC; CROSS-COUPLINGS; ELECTROPHILIC CARBON; N-HETEROCYCLIC CARBENE LIGANDS; STEREOSPECIFIC;

ESTERIFICATION; ESTERS; STEREOCHEMISTRY;

LIGANDS;

ARYLBORONIC ESTER; BENZYL ALCOHOL DERIVATIVE; BORON DERIVATIVE; CARBAMIC ACID DERIVATIVE; CARBENE; CARBON; GRIGNARD REAGENT; NICKEL; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CROSS CROUPLING REACTION; ELECTRON; ENANTIOMER; STEREOCHEMISTRY;

BENZYL COMPOUNDS; BORONIC ACIDS; CARBAMATES; CATALYSIS; ESTERS; METHANE; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 84874897652     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja311783k     Document Type: Article

References (61)

1. Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417
2. Lau, K. S. Y.; Fries, R. W.; Stille, J. K. J. Am. Chem. Soc. 1974, 96, 4983
3. Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 3910
4. Legros, J.-Y.; Toffano, M.; Fiaud, J.-C. Tetrahedron 1995, 51, 3235
5. Rodriquez, N.; de Arellano, C. R.; Asensio, G.; Medio-Simon, M. Chem.-Eur. J. 2007, 13, 4223
6. Lopez-Perez, A.; Adrio, J.; Carretero, J. C. Org. Lett. 2009, 11, 5514
7. He, A.; Falck, J. R. J. Am. Chem. Soc. 2010, 132, 2524
8. Rudolph, A.; Rackelmann, N.; Lautens, M. Angew. Chem., Int. Ed. 2007, 46, 1485
9. Trost, B. M.; VanVranken, D. L. Chem. Rev. 1996, 96, 395
10. Stille, J. K.; Cowell, A. B. J. Organomet. Chem. 1977, 124, 253
11. Saito, B.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 6694
12. Wilsily, A.; Tramutola, F.; Owston, N. A.; Fu, G. C. J. Am. Chem. Soc. 2012, 134, 5794 and references cited therein
13. Glorius, F. Angew. Chem., Int. Ed. 2008, 47, 8347
14. For a discussion, see: Molander, G. A.; Wisniewski, S. R. J. Am. Chem. Soc. 2012, 134, 16856
15. Bock, P. L.; Boschetto, D. J.; Rasmussen, J. R.; Demers, J. P.; Whitesides, G. M. J. Am. Chem. Soc. 1974, 96, 2814
16. Ridgway, B. H.; Woerpel, K. A. J. Org. Chem. 1998, 63, 458
17. Matos, K.; Soderquist, J. A. J. Org. Chem. 1998, 63, 461
18. Taylor, B. L. H.; Jarvo, E. R. J. Org. Chem. 2011, 76, 7573
19. Ye, J.; Bhatt, R. K.; Falck, J. R. J. Am. Chem. Soc. 1994, 116, 1
20. Hölzer, B.; Hoffmann, R. W. Chem. Commun. 2003, 732
21. Campos, K. R.; Klapars, A.; Waldman, J. H.; Dormer, P. G.; Chen, C.-Y. J. Am. Chem. Soc. 2006, 128, 3538
22. Lange, H.; Fröhlich, R.; Hoppe, D. Tetrahedron 2008, 64, 9123
23. Imao, D.; Glasspoole, B. W.; Laberge, S. V.; Crudden, C. M. J. Am. Chem. Soc. 2009, 131, 5024
24. Li, H.; He, A.; Falck, J. R.; Liebeskind, L. S. Org. Lett. 2011, 13, 3682
25. LaBadie, J. W.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 669
26. Kells, K. W.; Chong, J. M. J. Am. Chem. Soc. 2004, 126, 15666
27. Sandrock, D. L.; Jean-Gérard, L.; Chen, C.-Y.; Dreher, S. D.; Molander, G. A. J. Am. Chem. Soc. 2010, 132, 17108
28. Ohmura, T.; Awano, T.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 13191
29. Lee, J. C. H.; McDonald, R.; Hall, D. G. Nat. Chem. 2011, 3, 894
30. Hatanaka, Y.; Hiyama, T. J. Am. Chem. Soc. 1990, 112, 7793
31. Hiyama, T. J. Organomet. Chem. 2002, 653, 58
32. Awano, T.; Ohmura, T.; Suginome, M. J. Am. Chem. Soc. 2011, 133, 20738
33. Reference 9d.
34. Stymiest, J. L.; Bagutski, V.; French, R. M.; Aggarwal, V. M. Nature 2008, 456, 778
35. Taylor, B. L. H.; Swift, E. C.; Waetzig, J. D.; Jarvo, E. R. J. Am. Chem. Soc. 2011, 133, 389
36. Taylor, B. L. H.; Harris, M. R.; Jarvo, E. R. Angew. Chem., Int. Ed. 2012, 51, 7790
37. Greene, M. A.; Yonova, I. M.; Williams, F. J.; Jarvo, E. R. Org. Lett. 2012, 14, 4293
38. For a review, see: Taylor, B. L. H.; Jarvo, E. R. Synlett 2011, 2761
39. Beaver, M. G.; Jamison, T. F. Org. Lett. 2011, 13, 4140
40. Sylvester, K. T.; Wu, K.; Doyle, A. G. J. Am. Chem. Soc. 2012, 134, 9541
41. Lin, B. L.; Clough, C. R.; Hillhouse, G. L. J. Am. Chem. Soc. 2002, 124, 2890
42. Palchaudhuri, R.; Nesterenko, V.; Hergenrother, P. J. J. Am. Chem. Soc. 2008, 130, 10274
43. Shagufta; Srivastava, A. K.; Sharma, R.; Mishra, R.; Balapure, A. K.; Murthy, P. S. R.; Panda, G. Bioorg. Med. Chem. 2006, 14, 1497
44. Parai, M. K.; Panda, G.; Chaturvedi, V.; Manju, Y. K.; Sinha, S. Bioorg. Med. Chem. Lett. 2008, 18, 289
45. Ellsworth, B. A.; Ewing, W. R.; Jurica, E. U.S. Patent Appl. 2011/0082165A1, Apr 7, 2011.
46. Baba, K.; Maeda, K.; Tabata, Y.; Doi, M.; Kozawa, M. Chem. Pharm. Bull. 1988, 36, 2977
47. Herron, N.; Johansson, G. A.; Radu, N. S. U.S. Patent Appl. 2005/0187364, Aug 25, 2005.
48. Xu, Y.-Q.; Lu, J.-M.; Li, N.-J.; Yan, F.; Xia, X.; Xu, Q. Eur. Polym. J. 2008, 44, 2404
49. Breslow, R.; Chu, W. J. Am. Chem. Soc. 1973, 95, 411
50. Finocchiaro, P.; Gust, D.; Mislow, K. J. Am. Chem. Soc. 1974, 96, 3198
51. Duxbury, D. F. Chem. Rev. 1993, 93, 381
52. Zhang, J.; Bellomo, A.; Creamer, A. D.; Dreher, S. D.; Walsh, P. J. J. Am. Chem. Soc. 2012, 134, 13765
53. Yu, J.-Y.; Kuwano, R. Org. Lett. 2008, 10, 973
54. Molander, G. A.; Elia, M. D. J. Org. Chem. 2006, 71, 9198
55. Li, Y.-Z.; Li, B.-J.; Lu, X.-Y.; Lin, S.; Shi, Z.-J. Angew. Chem., Int. Ed. 2009, 48, 3817
56. Iovel, I.; Mertins, K.; Kischel, J.; Zapf, A.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 3913
57. For a representative Freidel-Crafts strategy, see: Esquivias, J.; Arrayás, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2006, 45, 629
58. Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882
59. Sun, F.-L.; Zheng, X.-J.; Gu, Q.; He, Q.-L.; You, S.-L. Eur. J. Org. Chem. 2010, 47
60. For es, see: Denmark, S. E.; Vogler, T. Chem.-Eur. J 2009, 15, 11737
61. 3 ligands, see: Clavier, H.; Nolan, S. P. Chem. Commun. 2010, 46, 841