Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Alkyl Bromides: Et3N as the Terminal Reductant

Organic Letters

Volumn 18, Issue 16, 2016, Pages 4012-4015

  Duan, Zhengli ^a   Li, Wu ^a   Lei, Aiwen ^a  

^a WUHAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84983262112     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.6b01837     Document Type: Article

References (81)

1. Weix, D. J. Acc. Chem. Res. 2015, 48, 1767-1775 10.1021/acs.accounts.5b00057
2. Gu, J.; Wang, X.; Xue, W.; Gong, H. Org. Chem. Front. 2015, 2, 1411-1421 10.1039/C5QO00224A
3. Knappke, C. E.; Grupe, S.; Gartner, D.; Corpet, M.; Gosmini, C.; Jacobi von Wangelin, A. Chem.-Eur. J. 2014, 20, 6828-6842 10.1002/chem.201402302
4. Everson, D. A.; Jones, B. A.; Weix, D. J. J. Am. Chem. Soc. 2012, 134, 6146-6159 10.1021/ja301769r
5. Anka-Lufford, L. L.; Prinsell, M. R.; Weix, D. J. J. Org. Chem. 2012, 77, 9989-10000 10.1021/jo302086g
6. Biswas, S.; Weix, D. J. J. Am. Chem. Soc. 2013, 135, 16192-16197 10.1021/ja407589e
7. Everson, D. A.; Buonomo, J. A.; Weix, D. J. Synlett 2014, 25, 233-238 10.1055/s-0033-1340151
8. Wotal, A. C.; Ribson, R. D.; Weix, D. J. Organometallics 2014, 33, 5874-5881 10.1021/om5004682
9. Ackerman, L. K.; Anka-Lufford, L. L.; Naodovic, M.; Weix, D. J. Chem. Sci. 2015, 6, 1115-1119 10.1039/C4SC03106G
10. Ackerman, L. K.; Lovell, M. M.; Weix, D. J. Nature 2015, 524, 454-457 10.1038/nature14676
11. Huihui, K. M.; Caputo, J. A.; Melchor, Z.; Olivares, A. M.; Spiewak, A. M.; Johnson, K. A.; DiBenedetto, T. A.; Kim, S.; Ackerman, L. K.; Weix, D. J. J. Am. Chem. Soc. 2016, 138, 5016-5019 10.1021/jacs.6b01533
12. Wang, S.; Qian, Q.; Gong, H. Org. Lett. 2012, 14, 3352-3355 10.1021/ol3013342
13. Wang, X.; Wang, S.; Xue, W.; Gong, H. J. Am. Chem. Soc. 2015, 137, 11562-11565 10.1021/jacs.5b06255
14. Jia, X.; Zhang, X.; Qian, Q.; Gong, H. Chem. Commun. 2015, 51, 10302-10305 10.1039/C5CC03113C
15. Molander, G. A.; Traister, K. M.; O'Neill, B. T. J. Org. Chem. 2014, 79, 5771-5780 10.1021/jo500905m
16. Molander, G. A.; Wisniewski, S. R.; Traister, K. M. Org. Lett. 2014, 16, 3692-3695 10.1021/ol501495d
17. Molander, G. A.; Traister, K. M.; O'Neill, B. T. J. Org. Chem. 2015, 80, 2907-2911 10.1021/acs.joc.5b00135
18. Fillon, H.; Gosmini, C.; Perichon, J. J. Am. Chem. Soc. 2003, 125, 3867-3870 10.1021/ja0289494
19. Qian, X.; Auffrant, A.; Felouat, A.; Gosmini, C. Angew. Chem., Int. Ed. 2011, 50, 10402-10405 10.1002/anie.201104390
20. Moncomble, A.; Le Floch, P.; Lledos, A.; Gosmini, C. J. Org. Chem. 2012, 77, 5056-5062 10.1021/jo3005149
21. Amatore, M.; Gosmini, C. Chem.-Eur. J. 2010, 16, 5848-5852 10.1002/chem.201000178
22. Duplais, C.; Krasovskiy, A.; Wattenberg, A.; Lipshutz, B. H. Chem. Commun. 2010, 46, 562-564 10.1039/B922280D
23. Krasovskiy, A.; Duplais, C.; Lipshutz, B. H. Org. Lett. 2010, 12, 4742-4744 10.1021/ol101885t
24. Dai, Y.; Wu, F.; Zang, Z.; You, H.; Gong, H. Chem.-Eur. J. 2012, 18, 808-812 10.1002/chem.201102984
25. Gosmini, C.; Bégouin, J.; Claudel, S. Synlett 2009, 2009, 3192-3194 10.1055/s-0029-1218307
26. Begouin, J. M.; Rivard, M.; Gosmini, C. Chem. Commun. 2010, 46, 5972-5974 10.1039/c0cc01055c
27. Gomes, P.; Gosmini, C.; Perichon, J. Org. Lett. 2003, 5, 1043-1045 10.1021/ol0340641
28. Li, X.; Feng, Z.; Jiang, Z. X.; Zhang, X. Org. Lett. 2015, 17, 5570-5573 10.1021/acs.orglett.5b02716
29. Moncomble, A.; Le Floch, P.; Gosmini, C. Chem.-Eur. J. 2009, 15, 4770-4774 10.1002/chem.200900542
30. Amatore, M.; Gosmini, C. Angew. Chem., Int. Ed. 2008, 47, 2089-2092 10.1002/anie.200704402
31. Krasovskaya, V.; Krasovskiy, A.; Bhattacharjya, A.; Lipshutz, B. H. Chem. Commun. 2011, 47, 5717-5719 10.1039/c1cc11087j
32. Yan, C.; Peng, Y.; Xu, X.; Wang, Y. Chem.-Eur. J. 2012, 18, 6039-6048 10.1002/chem.201200190
33. Peng, Y.; Xu, X.; Xiao, J.; Wang, Y. Chem. Commun. 2014, 50, 472-474 10.1039/C3CC47780K
34. Murphy, J. J.; Melchiorre, P. Nature 2015, 524, 297-298 10.1038/nature15200
35. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. Chem. Rev. 2013, 113, 5322-5363 10.1021/cr300503r
36. Chen, J. R.; Hu, X. Q.; Lu, L. Q.; Xiao, W. J. Chem. Soc. Rev. 2016, 45, 2044 10.1039/C5CS00655D
37. Skubi, K. L.; Yoon, T. P. Nature 2014, 515, 45-46 10.1038/515045a
38. Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527-532 10.1038/nchem.687
39. Narayanam, J. M.; Stephenson, C. R. Chem. Soc. Rev. 2011, 40, 102-113 10.1039/B913880N
40. Tucker, J. W.; Stephenson, C. R. J. Org. Chem. 2012, 77, 1617-1622 10.1021/jo202538x
41. Beatty, J. W.; Stephenson, C. R. Acc. Chem. Res. 2015, 48, 1474-1484 10.1021/acs.accounts.5b00068
42. Xuan, J.; Zhang, Z. G.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 15632-15641 10.1002/anie.201505731
43. Nicewicz, D. A.; MacMillan, D. W. Science 2008, 322, 77-80 10.1126/science.1161976
44. Pirnot, M. T.; Rankic, D. A.; Martin, D. B.; MacMillan, D. W. Science 2013, 339, 1593-1596 10.1126/science.1232993
45. Terrett, J. A.; Clift, M. D.; MacMillan, D. W. J. Am. Chem. Soc. 2014, 136, 6858-6861 10.1021/ja502639e
46. Zuo, Z.; Ahneman, D. T.; Chu, L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. Science 2014, 345, 437-440 10.1126/science.1255525
47. Chu, L.; Lipshultz, J. M.; MacMillan, D. W. Angew. Chem., Int. Ed. 2015, 54, 7929-7933 10.1002/anie.201501908
48. Cuthbertson, J. D.; MacMillan, D. W. Nature 2015, 519, 74-77 10.1038/nature14255
49. Jin, J.; MacMillan, D. W. Nature 2015, 525, 87-90 10.1038/nature14885
50. Noble, A.; McCarver, S. J.; MacMillan, D. W. J. Am. Chem. Soc. 2015, 137, 624-627 10.1021/ja511913h
51. Terrett, J. A.; Cuthbertson, J. D.; Shurtleff, V. W.; MacMillan, D. W. Nature 2015, 524, 330-334 10.1038/nature14875
52. Zuo, Z.; Cong, H.; Li, W.; Choi, J.; Fu, G. C.; MacMillan, D. W. J. Am. Chem. Soc. 2016, 138, 1832-1835 10.1021/jacs.5b13211
53. Ischay, M. A.; Lu, Z.; Yoon, T. P. J. Am. Chem. Soc. 2010, 132, 8572-8574 10.1021/ja103934y
54. Farney, E. P.; Yoon, T. P. Angew. Chem., Int. Ed. 2014, 53, 793-797 10.1002/anie.201308820
55. Du, J.; Skubi, K. L.; Schultz, D. M.; Yoon, T. P. Science 2014, 344, 392-396 10.1126/science.1251511
56. Narayanam, J. M.; Tucker, J. W.; Stephenson, C. R. J. Am. Chem. Soc. 2009, 131, 8756-8757 10.1021/ja9033582
57. Furst, L.; Matsuura, B. S.; Narayanam, J. M.; Tucker, J. W.; Stephenson, C. R. Org. Lett. 2010, 12, 3104-3107 10.1021/ol101146f
58. Nguyen, J. D.; D'Amato, E. M.; Narayanam, J. M.; Stephenson, C. R. Nat. Chem. 2012, 4, 854-859 10.1038/nchem.1452
59. Wallentin, C. J.; Nguyen, J. D.; Finkbeiner, P.; Stephenson, C. R. J. Am. Chem. Soc. 2012, 134, 8875-8884 10.1021/ja300798k
60. Bergonzini, G.; Schindler, C. S.; Wallentin, C. J.; Jacobsen, E. N.; Stephenson, C. R. Chem. Sci. 2014, 5, 112 10.1039/C3SC52265B
61. Douglas, J. J.; Albright, H.; Sevrin, M. J.; Cole, K. P.; Stephenson, C. R. Angew. Chem., Int. Ed. 2015, 54, 14898-14902 10.1002/anie.201507369
62. Meng, Q. Y.; Zhong, J. J.; Liu, Q.; Gao, X. W.; Zhang, H. H.; Lei, T.; Li, Z. J.; Feng, K.; Chen, B.; Tung, C. H.; Wu, L. Z. J. Am. Chem. Soc. 2013, 135, 19052-19055 10.1021/ja408486v
63. Wang, L.; Wei, X. J.; Jia, W. L.; Zhong, J. J.; Wu, L. Z.; Liu, Q. Org. Lett. 2014, 16, 5842-5845 10.1021/ol502676y
64. Zhang, G.; Liu, C.; Yi, H.; Meng, Q.; Bian, C.; Chen, H.; Jian, J. X.; Wu, L. Z.; Lei, A. J. Am. Chem. Soc. 2015, 137, 9273-9280 10.1021/jacs.5b05665
65. Liu, J.; Liu, Q.; Yi, H.; Qin, C.; Bai, R.; Qi, X.; Lan, Y.; Lei, A. Angew. Chem., Int. Ed. 2014, 53, 502-506 10.1002/anie.201308614
66. Guo, W.; Lu, L. Q.; Wang, Y.; Wang, Y. N.; Chen, J. R.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 2265-2269 10.1002/anie.201408837
67. Griffin, J. D.; Zeller, M. A.; Nicewicz, D. A. J. Am. Chem. Soc. 2015, 137, 11340-11348 10.1021/jacs.5b07770
68. Romero, N. A.; Margrey, K. A.; Tay, N. E.; Nicewicz, D. A. Science 2015, 349, 1326-1330 10.1126/science.aac9895
69. Perkowski, A. J.; You, W.; Nicewicz, D. A. J. Am. Chem. Soc. 2015, 137, 7580-7583 10.1021/jacs.5b03733
70. Nakajima, M.; Fava, E.; Loescher, S.; Jiang, Z.; Rueping, M. Angew. Chem., Int. Ed. 2015, 54, 8828-8832 10.1002/anie.201501556
71. Sahoo, B.; Li, J. L.; Glorius, F. Angew. Chem., Int. Ed. 2015, 54, 11577-11580 10.1002/anie.201503210
72. Gui, Y.-Y.; Sun, L.; Lu, Z.-P.; Yu, D.-G. Org. Chem. Front. 2016, 3, 522-526 10.1039/C5QO00437C
73. Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433-436 10.1126/science.1253647
74. Amani, J.; Sodagar, E.; Molander, G. A. Org. Lett. 2016, 18, 732-735 10.1021/acs.orglett.5b03705
75. Jouffroy, M.; Kelly, C. B.; Molander, G. A. Org. Lett. 2016, 18, 876-879 10.1021/acs.orglett.6b00208
76. Jouffroy, M.; Primer, D. N.; Molander, G. A. J. Am. Chem. Soc. 2016, 138, 475-478 10.1021/jacs.5b10963
77. Tasker, S. Z.; Jamison, T. F. J. Am. Chem. Soc. 2015, 137, 9531-9534 10.1021/jacs.5b05597
78. Skubi, K. L.; Blum, T. R.; Yoon, T. P. Chem. Rev. 2016, DOI: 10.1021/acs.chemrev.6b00018.
79. Ryu, D.; Primer, D. N.; Tellis, J. C.; Molander, G. A. Chem.-Eur. J. 2016, 22, 120-123 10.1002/chem.201504079
80. Pratsch, G.; Overman, L. E. J. Org. Chem. 2015, 80, 11388-11397 10.1021/acs.joc.5b01962
81. During the preparation of this manuscript, Prof. David W. C. MacMillan reported one silyl radical activation of alkyl halides in metallaphotoredox catalysis. Zhang, P.; Le, C. C.; MacMillan, D. W. J. Am. Chem. Soc. 2016, 138, 8084-8087 10.1021/jacs.6b04818