Reductive cross-coupling of conjugated arylalkenes and aryl bromides with hydrosilanes by cooperative palladium/copper catalysis

Angewandte Chemie - International Edition

Volumn 55, Issue 21, 2016, Pages 6275-6279

  Semba, Kazuhiko ^a   Ariyama, Kenta ^a   Zheng, Hong ^b   Kameyama, Ryohei ^a   Sakaki, Shigeyoshi ^b   Nakao, Yoshiaki ^a  

^a KYOTO UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

alkenes; alkynes; copper; cross coupling; palladium

Indexed keywords

CATALYSIS; COPPER; HYDROCARBONS; METAL HALIDES; OLEFINS; PALLADIUM;

ALKYNES; ARYL BROMIDES; BIOLOGICALLY ACTIVE MOLECULES; CROSS-COUPLINGS; INTERNAL ALKYNES; REACTION CONDITIONS; REGIO-SELECTIVE; TRISUBSTITUTED ALKENES;

CHEMICAL REACTIONS;

EID: 84963606500     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201511975     Document Type: Article

References (63)

1. N. Miyaura, Top. Curr. Chem. 2002, 219, 11;
2. T. Hiyama, E. Shirakawa, Top. Curr. Chem. 2002, 219, 61;
3. K. Fugami, M. Kosugi, Top. Curr. Chem. 2002, 219, 87;
4. "Palladium-Catalyzed Reactions Involving Reductive Elimination": Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1 (Ed.:, E. Negishi,), Wiley, New York, 2002, pp. 215-994;
5. R. Jana, T. P. Pathak, M. S. Sigman, Chem. Rev. 2011, 111, 1417;
6. J. Terao, N. Kambe, Acc. Chem. Res. 2008, 41, 1545;
7. E. Negishi, G. Wang, H. Rao, Z. Xu, J. Org. Chem. 2010, 75, 3151.
8. B. M. Trost, Z. T. Ball, Synthesis 2005, 853;
9. Modern Reduction Methods (Eds.:, P. G. Andersson, I. J. Munslow,), Wiley-VCH, Weinheim, 2008.
10. E. P. Jackson, H. A. Malik, G. J. Sormunen, R. D. Baxter, P. Liu, H. Wang, A.-R. Shareef, J. Montgomery, Acc. Chem. Res. 2015, 48, 1736;
11. E. Skucas, M.-Y. Ngai, V. Komanduri, M. J. Krische, Acc. Chem. Res. 2007, 40, 1394;
12. H.-Y. Jang, M. J. Krische, Acc. Chem. Res. 2004, 37, 653.
13. Y. Hatanaka, T. Hiyama, J. Am. Chem. Soc. 1990, 112, 7793;
14. D. Imao, B. W. Glasspoole, V. S. Laberge, C. M. Crudden, J. Am. Chem. Soc. 2009, 131, 5024;
15. B. W. Glasspoole, M. S. Oderinde, B. D. Moore, A. Antoft-Finch, C. M. Crudden, Synthesis 2013, 1759;
16. M. A. Schade, A. Metzger, S. Hug, P. Knochel, Chem. Commun. 2008, 3046;
17. C. I. Someya, S. Inoue, S. Krackl, E. Irran, S. Enthaler, Eur. J. Inorg. Chem. 2012, 1269.
18. K. Srinivas, N. Srinivasan, K. S. Reddy, M. Ramakrishna, C. R. Reddy, M. Arunagiri, R. L. Kumari, S. Venkataraman, V. T. Mathad, Org. Process Res. Dev. 2005, 9, 314;
19. K. Vukics, T. Fodor, J. Fischer, I. Fellegvári, S. Lévai, Org. Process Res. Dev. 2002, 6, 82;
20. M. Alami, S. Messaoudi, A. Hamze, O. Provot, J.-D. Brion, J.-M. Liu, J. Bignon, J. Bakala, Patent WO/2009/147217 A1, Dec 10, 2009.
21. T. Hayashi, Y. Matsumoto, Y. Ito, J. Am. Chem. Soc. 1989, 111, 3426;
22. C. M. Crudden, Y. B. Hleba, A. C. Chen, J. Am. Chem. Soc. 2004, 126, 9200;
23. D. Noh, H. Chea, J. Ju, J. Yun, Angew. Chem. Int. Ed. 2009, 48, 6062;
24. Angew. Chem. 2009, 121, 6178; for selected references on the hydrosilylation of styrenes, see
25. T. Hayashi, K. Tamao, Y. Katsuro, I. Nakae, M. Kumada, Tetrahedron Lett. 1980, 21, 1871;
26. K. Kitayama, Y. Uozumi, T. Hayashi, J. Chem. Soc. Chem. Commun. 1995, 1533.
27. K. M. Gligorich, S. A. Cummings, M. S. Sigman, J. Am. Chem. Soc. 2007, 129, 14193;
28. Y. Iwai, K. M. Gligorich, M. S. Sigman, Angew. Chem. Int. Ed. 2008, 47, 3219;
29. Angew. Chem. 2008, 120, 3263;
30. K. M. Gligorich, Y. Iwai, S. A. Cummings, M. S. Sigman, Tetrahedron 2009, 65, 5074.
31. K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467;
32. L. S. Liebeskind, R. W. Fengl, J. Org. Chem. 1990, 55, 5359;
33. J. Huang, J. Chan, Y. Chen, C. J. Borths, K. D. Baucom, R. D. Larsen, M. M. Faul, J. Am. Chem. Soc. 2010, 132, 3674;
34. F. Nahra, Y. Macé, D. Lambin, O. Riant, Angew. Chem. Int. Ed. 2013, 52, 3208;
35. Angew. Chem. 2013, 125, 3290;
36. S. Vercruysse, L. Cornelissen, F. Nahra, L. Collard, O. Riant, Chem. Eur. J. 2014, 20, 1834;
37. F. Nahra, Y. Macé, A. Boreux, F. Billard, O. Riant, Chem. Eur. J. 2014, 20, 10970;
38. K. B. Smith, K. M. Logan, W. You, M. K. Brown, Chem. Eur. J. 2014, 20, 12032;
39. K. M. Logan, K. B. Smith, M. K. Brown, Angew. Chem. Int. Ed. 2015, 54, 5228;
40. Angew. Chem. 2015, 127, 5317.
41. K. Semba, Y. Nakao, J. Am. Chem. Soc. 2014, 136, 7567; the arylboration of alkenes was independently reported Brown and co-workers, see
42. N. P. Mankad, D. S. Laitar, J. P. Sadighi, Organometallics 2004, 23, 3369; the hydrocupration of styrenes has been proposed in the context of hydroboration and hydroamination of styrene derivatives, see
43. Y. Miki, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 2013, 52, 10830;
44. Angew. Chem. 2013, 125, 11030;
45. S. Zhu, N. Niljianskul, S. L. Buchwald, J. Am. Chem. Soc. 2013, 135, 15746;
46. Y.-M. Wang, N. C. Bruno, Á. L. Placeres, S. Zhu, S. L. Buchwald, J. Am. Chem. Soc. 2015, 137, 10524.
47. N. Jabri, A. Alexakis, J. F. Normant, Tetrahedron Lett. 1981, 22, 959.
48. F. Ozawa, T. Ito, Y. Nakamura, A. Yamamoto, Bull. Chem. Soc. Jpn. 1981, 54, 1868;
49. K. Tatsumi, R. Hoffmann, A. Yamamoto, J. K. Stille, Bull. Chem. Soc. Jpn. 1981, 54, 1857.
50. D. Noh, S. K. Yoon, J. Won, J. Y. Lee, J. Yun, Chem. Asian J. 2011, 6, 1967;
51. J. Won, D. Noh, J. Yun, Y. Lee, J. Phys. Chem. A 2010, 114, 12112.
52. J. W. Labadie, J. K. Stille, J. Am. Chem. Soc. 1983, 105, 6129;
53. K. W. Kells, J. M. Chong, J. Am. Chem. Soc. 2004, 126, 15666;
54. T. Ohmura, T. Awano, M. Suginome, J. Am. Chem. Soc. 2010, 132, 13191;
55. D. L. Sandrock, L. Jean-Gérard, C. Chen, S. D. Dreher, G. A. Molander, J. Am. Chem. Soc. 2010, 132, 17108;
56. J. C. H. Lee, R. McDonald, D. G. Hall, Nat. Chem. 2011, 3, 894;
57. L. Li, S. Zhao, A. Joshi-Pangu, M. Diane, M. R. Biscoe, J. Am. Chem. Soc. 2014, 136, 14027;
58. R. E. Maleczka, Jr., I. Terstiege, J. Org. Chem. 1998, 63, 9622;
59. R. E. Maleczka, Jr., W. P. Gallagher, I. Terstiege, J. Am. Chem. Soc. 2000, 122, 384;
60. W. P. Gallagher, I. Terstiege, R. E. Maleczka, Jr., J. Am. Chem. Soc. 2001, 123, 3194;
61. R. E. Maleczka, Jr., W. P. Gallagher, Org. Lett. 2001, 3, 4173;
62. W. P. Gallagher, R. E. Maleczka, Jr., J. Org. Chem. 2005, 70, 841.
63. 3 has been reported. However, the reaction exclusively affords anti-addition products:, D. W. Robbins, J. F. Hartwig, Science 2011, 333, 1423.