A palladium-catalyzed three-component cross-coupling of conjugated dienes or terminal alkenes with vinyl triflates and boronic acids

Journal of the American Chemical Society

Volumn 133, Issue 15, 2011, Pages 5784-5787

  Liao, Longyan ^a   Jana, Ranjan ^a   Urkalan, Kaveri Balan ^a   Sigman, Matthew S ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID; CONJUGATED DIENES; CROSS-COUPLINGS; DIFUNCTIONALIZATION; HYDRIDE ELIMINATION; TERMINAL ALKENES; THREE-COMPONENT; THREE-COMPONENT COUPLING; TRIFLATES;

CATALYSIS; REACTION INTERMEDIATES;

OLEFINS;

ALKENE DERIVATIVE; BORONIC ACID DERIVATIVE; PALLADIUM; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; ELIMINATION REACTION;

ALKENES; BORONIC ACIDS; CATALYSIS; MESYLATES; PALLADIUM; VINYL COMPOUNDS;

EID: 79954506539     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja201358b     Document Type: Article

References (62)

1. For reviews of the Heck reaction, see: Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009
2. Coeffard, V.; Guiry, P. J. Curr. Org. Chem. 2010, 14, 212
3. Narayanan, R. Molecules 2010, 15, 2124
4. Anon Chemtracts 2010, 23, 61
5. Punniyamurthy, T.; Velusamy, S.; Iqbal, J. Chem. Rev. 2005, 105, 2329
6. Feringa, B. L. Transition Met. Org. Synth. 1998, 2, 307
7. Cornell, C. N.; Sigman, M. S. Inorg. Chem. 2007, 46, 1903
8. Anderson, B. J., Keith, J. A., and Sigman, M. S. J. Am. Chem. Soc. 2010, 132, 11872 and references therein
9. For a review, see: Jensen, K. H.; Sigman, M. S. Org. Biomol. Chem. 2008, 6, 4083
10. Jensen, K. H.; Webb, J. D.; Sigman, M. S. J. Am. Chem. Soc. 2010, 132, 17471
11. Pathak, T. P.; Gligorich, K. M.; Welm, B. E.; Sigman, M. S. J. Am. Chem. Soc. 2010, 132, 7870
12. Werner, E. W.; Urkalan, K. B.; Sigman, M. S. Org. Lett. 2010, 12, 2848
13. Urkalan, K. B.; Sigman, M. S. Angew. Chem., Int. Ed. 2009, 48, 3146
14. Zhang, Y.; Sigman, M. S. J. Am. Chem. Soc. 2007, 129, 3076
15. Schultz, M. J.; Sigman, M. S. J. Am. Chem. Soc. 2006, 128, 1460
16. For examples of Pd-catalyzed alkene difunctionalization reactions under oxidative conditions, see: Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318
17. Liu, G.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 7179-7181
18. Li, Y.; Song, D.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2962
19. Wang, A.; Jiang, H.; Chen, H. J. Am. Chem. Soc. 2009, 131, 3846-3847
20. Qiu, S.; Xu, T.; Zhou, J.; Guo, Y.; Liu, G. J. Am. Chem. Soc. 2010, 132, 2856
21. Kalyani, D.; Satterfield, A. D.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 8419
22. For an example of palladium-catalyzed diarylation of a vinyl ether, see: Trejos, A.; Fardost, A.; Yahiaoui, S.; Larhed, M. Chem. Commun. 2009, 7587-7589
23. For diarylation of activated alkenes, see: Delample, M.; Villandier, N.; Douliez, J.-P.; Camy, S.; Condoret, J.-S.; Pouilloux, Y.; Barrault, J.; Jerome, F. Green Chem. 2010, 12, 804 and references cited therein
24. For examples of the formation of π-allyl-Pd intermediates by nucleophilic addition to a diene, see: Bäckvall, J. E.; Nystroem, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1985, 107, 3676
25. Bar, G. L. J.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2005, 127, 7308
26. Du, H.; Yuan, W.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 7496
27. Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2008, 130, 8590
28. Mino, T.; Kajiwara, K.; Shirae, Y.; Sakamoto, M.; Fujita, T. Synlett 2008, 2711
29. Denmark, S. E.; Werner, N. S. J. Am. Chem. Soc. 2008, 130, 16382
30. Zhao, B.; Du, H.; Cui, S.; Shi, Y. J. Am. Chem. Soc. 2010, 132, 3523
31. Zhang, X.; Larock, R. C. Tetrahedron 2010, 66, 4265
32. Liao, L.; Sigman, M. S. J. Am. Chem. Soc. 2010, 132, 10209
33. Zhang, P.; Brozek, L. A.; Morken, J. P. J. Am. Chem. Soc. 2010, 132, 10686
34. For the use of π-benzyl-Pd intermediates, see: Becker, Y.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 845
35. Nettekoven, U.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 1166
36. Lindsell, W. E.; Palmer, D. D.; Preston, P. N.; Rosair, G. M.; Jones, R. V. H.; Whitton, A. J. Organometallics 2005, 24, 1119
37. Johns, A. M.; Tye, J. W.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 16010
38. Narahashi, H.; Isao, S.; Yamamoto, A. J. Organomet. Chem. 2008, 693, 283
39. Torregrosa, R. R. P.; Ariyarathna, Y.; Chattopadhyay, K.; Tunge, J. A. J. Am. Chem. Soc. 2010, 132, 9280
40. Kuwano, R.; Kondo, Y.; Matsuyama, Y. J. Am. Chem. Soc. 2003, 125, 12104
41. Jutand, A.; Négri, S. Organometallics 2003, 22, 4229
42. Jutand, A.; Mosleh, A. Organometallics 1995, 14, 1810
43. For skipped diene synthesis, see: Braddock, D. C.; Badine, D. M.; Gottschalk, T. Synlett 2001, 1909
44. Thadani, A. N.; Rawal, V. H. Org. Lett. 2002, 4, 4317
45. Nájera, C. J. Org. Chem. 2009, 74, 2321
46. Torii, S.; Okumoto, H.; Ozaki, H.; Nakayasu, S.; Kotani, T. Tetrahedron Lett. 1990, 31, 5319
47. Torii, S.; Okumoto, H.; Kotani, T.; Nakayasu, S.; Ozaki, H. Tetrahedron Lett. 1992, 33, 3503
48. Shaulis, K. M.; Hoskin, B. L.; Townsend, J. R.; Goodson, F. E.; Incarvito, C. D.; Rheingold, A. L. J. Org. Chem. 2002, 67, 5860
49. Oh, C. H.; Lim, Y. M. Tetrahedron Lett. 2003, 44, 267
50. Zhou, C.; Larock, R. C. J. Org. Chem. 2005, 70, 3765
51. Jayanth, T. T.; Jeganmohan, M.; Cheng, C.-H. Org. Lett. 2005, 7, 2921
52. Cheng, Y.-n.; Duan, Z.; Yu, L.; Li, Z.; Zhu, Y.; Wu, Y. Org. Lett. 2008, 10, 901
53. Zhang, X.; Larock, R. C. Tetrahedron 2010, 66, 4265
54. Kudirka, R.; Devine, S. K. J.; Adams, C. S.; Van Vranken, D. L. Angew. Chem., Int. Ed. 2009, 48, 3677
55. Zhou, L.; Ye, F.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2010, 132, 13590
56. Huang, T.-H.; Chang, H.-M.; Wu, M.-Y.; Cheng, C.-H. J. Org. Chem. 2001, 67, 99
57. Aftab, T.; Grigg, R.; Ladlow, M.; Sridharan, V.; Thornton-Pett, M. Chem. Commun. 2002, 1754
58. Shu, W.; Jia, G.; Ma, S. Angew. Chem., Int. Ed. 2009, 48, 2788
59. For three-component couplings of this type with 1,3-dienes using other metals, see: Mizutani, K.; Shinokubo, H.; Oshima, K. Org. Lett. 2003, 5, 3959
60. Terao, J.; Nii, S.; Chowdhury, F. A.; Nakamura, A.; Kambe, N. Adv. Synth. Catal. 2004, 346, 905
61. Wayland, B. B.; Schramm, R. F. Inorg. Chem. 1969, 8, 971
62. Bueno, A. C.; de, S. A. O.; Gusevskaya, E. V. Adv. Synth. Catal. 2009, 351, 2491