Catalyst-controlled regioselectivity in the synthesis of branched conjugated dienes via aerobic oxidative heck reactions

Journal of the American Chemical Society

Volumn 134, Issue 40, 2012, Pages 16496-16499

  Zheng, Changwu ^a   Wang, Dian ^a   Stahl, Shannon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

C-C BOND FORMATION; COMPUTATIONAL STUDIES; CONJUGATED DIENES; HECK REACTIONS; NON-OXIDATIVE; OXIDATIVE COUPLINGS; REGIO-SELECTIVE; STERIC EFFECT; VINYL BROMIDES;

ALKENYLATION; BROMINE COMPOUNDS; CATALYSTS; LIGANDS; REGIOSELECTIVITY;

OLEFINS;

ALKADIENE; ALKENE DERIVATIVE; BORONIC ACID DERIVATIVE; CARBON; PHENANTHROLINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; DENSITY FUNCTIONAL THEORY; HECK REACTION; OXIDATION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

ALKENES; BORONIC ACIDS; CATALYSIS; OXIDATION-REDUCTION; PALLADIUM; POLYENES; STEREOISOMERISM;

EID: 84867339840     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja307371w     Document Type: Article

References (52)

1. Heck, R. F. Acc. Chem. Res. 1979, 12, 146
2. de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. 1995, 33, 2379
3. Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2
4. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009
5. Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945
6. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442
7. Nilsson, P.; Olofsson, K.; Larhed, M. In The Mizoroki-Heck Reaction; Oestreich, M., Ed.; John Wiley & Sons: Chichester, 2009; pp 133-162.
8. Karimi, B.; Behzadnia, H.; Elhamifar, D.; Akhavan, P. F.; Esfahani, F. K.; Zamani, A. Synthesis 2010, 1399
9. Mc Cartney, D.; Guiry, P. J. Chem. Soc. Rev. 2011, 40, 5122
10. Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083
11. Crisp, G. T.; Glink, P. T. Tetrahedron 1994, 50, 2623
12. Berthiol, F.; Doucet, H.; Santelli, M. Synlett 2003, 841
13. Yoon, C. H.; Yoo, K. S.; Yi, S. W.; Mishra, R. K.; Jung, K. W. Org. Lett. 2004, 6, 4037
14. Hansen, A. L.; Ebran, J. P.; Ahlquist, M.; Norrby, P. O.; Skrydstrup, T. Angew. Chem., Int. Ed. 2006, 45, 3349
15. Yoo, K. S.; Yoon, C. H.; Jung, K. W. J. Am. Chem. Soc. 2006, 128, 16384
16. Ebran, J.-P.; Hansen, A. L.; Gøgsig, T. M.; Skrydstrup, T. J. Am. Chem. Soc. 2007, 129, 6931
17. Lemhadri, M.; Battace, A.; Berthiol, F.; Zair, T.; Doucet, H.; Santelli, M. Synthesis 2008, 1142
18. Crisp, G. T.; Gebauer, M. G. Tetrahedron 1996, 52, 12465
19. Delcamp, J. H.; Brucks, A. P.; White, M. C. J. Am. Chem. Soc. 2008, 130, 11270
20. Pan, D.; Chen, A.; Su, Y.; Zhou, W.; Li, S.; Jia, W.; Xiao, J.; Liu, Q.; Zhang, L.; Jiao, N. Angew. Chem., Int. Ed. 2008, 47, 4729
21. Su, Y.; Jiao, N. Org. Lett. 2009, 11, 2980
22. Vallin, K. S. A.; Zhang, Q. S.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 2003, 68, 6639
23. Hansen, A. L.; Skrydstrup, T. Org. Lett. 2005, 7, 5585
24. McConville, M.; Saidi, O.; Blacker, J.; Xiao, J. J. Org. Chem. 2009, 74, 2692
25. Andappan, M. M. S.; Nilsson, P.; von Schenck, H.; Larhed, M. J. Org. Chem. 2004, 69, 5212
26. Ruan, J.; Xiao, J. Acc. Chem. Res. 2011, 44, 614 and the references cited
27. Patel, B. A.; Heck, R. F. J. Org. Chem. 1978, 43, 3898
28. Kim, J.; Lee, J. T.; Yeo, K. D. Bull. Korean Chem. Soc. 1985, 6, 366
29. Wang, G.; Mohan, S.; Negishi, E. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 11344
30. Werner, E. W.; Sigman, M. S. J. Am. Chem. Soc. 2010, 132, 13981
31. Werner, E. W.; Sigman, M. S. J. Am. Chem. Soc. 2011, 133, 9692
32. Qin, L. N.; Ren, X. F.; Lu, Y. P.; Li, Y. X.; Zhou, J. R. Angew. Chem., Int. Ed. 2012, 51, 5915
33. A recent Ni-catalyzed Heck-type coupling of benzyl chlorides and alkenes exhibits selectivity for the branched isomer: Matsubara, R.; Gutierrez, A. C.; Jamison, T. F. J. Am. Chem. Soc. 2011, 133, 19020
34. Mo, J.; Xu, L.; Xiao, J. J. Am. Chem. Soc. 2005, 127, 751
35. Mo, J.; Xu, L.; Ruan, J.; Liu, S.; Xiao, J. Chem. Commun. 2006, 3591
36. Campbell, A. N.; White, P. B.; Guzei, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2010, 132, 15116
37. Izawa, Y.; Stahl, S. S. Adv. Synth. Catal. 2010, 352, 3223
38. Campbell, A. N.; Meyer, E. B.; Stahl, S. S. Chem. Commun. 2011, 10257
39. Andappan, M. M. S.; Nilsson, P.; Larhed, M. Chem. Commun. 2004, 218
40. Enquist, P. A.; Lindh, J.; Nilsson, P.; Larhed, M. Green Chem. 2006, 8, 338
41. Lindh, J.; Enquist, P. A.; Pilotti, Å.; Nilsson, P.; Larhed, M. J. Org. Chem. 2007, 72, 7957
42. See ref 2f and the following: Yoo, K. S.; Park, C. P.; Yoon, C. H.; Sakaguchi, S.; O'Neill, J.; Jung, K. W. Org. Lett. 2007, 9, 3933
43. Park, C. P.; Kim, D.-P. J. Am. Chem. Soc. 2010, 132, 10102
44. Gottumukkala, A. L.; Teichert, J. F.; Heijnen, D.; Eisink, N.; van Dijk, S.; Ferrer, C.; van den Hoogenband, A.; Minnaard, A. J. J. Org. Chem. 2011, 76, 3498
45. 2 substrates: Jung, Y. C.; Mishra, R. K.; Yoon, C. H.; Jung, K. W. Org. Lett. 2003, 5, 2231
46. Stahl, S. S.; Thorman, J. L.; Nelson, R. C.; Kozee, M. A. J. Am. Chem. Soc. 2001, 123, 7188
47. Popp, B. V.; Morales, C. M.; Landis, C. R.; Stahl, S. S. Inorg. Chem. 2010, 49, 8200
48. Cabri, W.; Candiani, I.; Bedeschi, A. J. Org. Chem. 1993, 58, 7421
49. See ref 20 and the following: Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. Synlett 1992, 871
50. Reetz, M. T.; Westermann, E. Angew. Chem., Int. Ed. 2000, 39, 165
51. de Vries, J. G. Dalton Trans. 2006, 421
52. Reetz, M. T.; de Vries, J. G. Chem. Commun. 2004, 1559