Nickel-catalyzed alkynylation of anisoles via C-O bond cleavage

Organic Letters

Volumn 17, Issue 3, 2015, Pages 680-683

  Tobisu, Mamoru ^a   Takahira, Tsuyoshi ^a   Ohtsuki, Akimichi ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84922607835     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol503707m     Document Type: Article

References (76)

1. Topics in Current Chemistry; Miyaura, N., Ed.; Wiley: Chichester, 2001; Vol. 219.
2. De Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; Wiley-VCH: Weinheim, Germany, 2004.
3. Yu, D.-G.; Li, B.-J.; Shi, Z.-J. Acc. Chem. Res. 2010, 43, 1486
4. Li, B.-J.; Yu, D.-G.; Sun, C.-L.; Shi, Z.-J. Chem.-Eur. J. 2011, 17, 1728
5. Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.-M.; Garg, N. K.; Percec, V. Chem. Rev. 2011, 111, 1346
6. Mesganaw, T.; Garg, N. K. Org. Process Res. Dev. 2013, 17, 29
7. Tobisu, M.; Chatani, N. Top. Organomet. Chem. 2013, 44, 35
8. Yamaguchi, J.; Muto, K.; Itami, K. Eur. J. Org. Chem. 2013, 19
9. Han, F.-S. Chem. Soc. Rev. 2013, 42, 5270
10. Cornella, J.; Zarate, C.; Martin, R. Chem. Soc. Rev. 2014, 43, 8081
11. Yu, D.-G.; Li, B.-J.; Zheng, S.-F.; Guan, B.-T.; Wang, B.-Q.; Shi, Z.-J. Angew. Chem., Int. Ed. 2010, 49, 4566
12. Yu, D.-G.; Shi, Z.-J. Angew. Chem., Int. Ed. 2011, 50, 7097
13. Murai, M.; Origuchi, K.; Takai, K. Org. Lett. 2014, 16, 3828
14. Wenkert, E.; Michelotti, E. L.; Swindell, C. S. J. Am. Chem. Soc. 1979, 101, 2246
15. Wenkert, E.; Michelotti, E. L.; Swindell, C. S.; Tingoli, M. J. Org. Chem. 1984, 49, 4894
16. Dankwardt, J. W. Angew. Chem., Int. Ed. 2004, 43, 2428
17. Guan, B.-T.; Xiang, S.-K.; Wu, T.; Sun, Z.-P.; Wang, B.-Q.; Zhao, K.-Q.; Shi, Z.-J. Chem. Commun. 2008, 1437
18. Guan, B.-T.; Xiang, S.-K.; Wang, B.-Q.; Sun, Z.-P.; Wang, Y.; Zhao, K.-Q.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 3268
19. Taylor, B. L. H.; Swift, E. C.; Waetzig, J. D.; Jarvo, E. R. J. Am. Chem. Soc. 2011, 133, 389
20. Xie, L.-G.; Wang, Z.-X. Chem.-Eur. J. 2011, 17, 4972
21. Zhao, F.; Yu, D.-G.; Zhu, R.-Y.; Xi, Z.; Shi, Z. J. Chem. Lett. 2011, 40, 1001
22. Iglesias, M. J.; Prieto, A.; Nicasio, M. C. Org. Lett. 2012, 14, 4318
23. Zhao, F.; Zhang, Y.-F.; Wen, J.; Yu, D.-G.; Wei, J.-B.; Xi, Z.; Shi, Z.-J. Org. Lett. 2013, 15, 3230
24. Cornella, J.; Martin, R. Org. Lett. 2013, 15, 6298
25. Yonova, I. M.; Johnson, A. G.; Osborne, C. A.; Moore, C. E.; Morrissette, N. S.; Jarvo, E. R. Angew. Chem., Int. Ed. 2014, 53, 2422
26. Iwasaki, T.; Miyata, Y.; Akimoto, R.; Fujii, Y.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2014, 136, 9260
27. Cross-coupling with trimethylsilyl lithium: Leiendecker, M.; Hsiao, C.-C.; Guo, L.; Alandini, N.; Rueping, M. Angew. Chem., Int. Ed. 2014, 53, 12912
28. Cross-coupling with organozinc reagents: Wang, C.; Ozaki, T.; Takita, R.; Uchiyama, M. Chem.-Eur. J. 2012, 18, 3482
29. Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2004, 126, 2706
30. Ueno, S.; Mizushima, E.; Chatani, N.; Kakiuchi, F. J. Am. Chem. Soc. 2006, 128, 16516
31. Tobisu, M.; Shimasaki, T.; Chatani, N. Angew. Chem., Int. Ed. 2008, 47, 4866
32. Shimasaki, T.; Konno, Y.; Tobisu, M.; Chatani, N. Org. Lett. 2009, 11, 4890
33. Tobisu, M.; Yasutome, A.; Kinuta, H.; Nakamura, K. Org. Lett. 2014, 16, 5572
34. Tobisu, M.; Shimasaki, T.; Chatani, N. Chem. Lett. 2009, 38, 710
35. Tobisu, M.; Yasutome, A.; Yamakawa, K.; Shimasaki, T.; Chatani, N. Tetrahedron 2012, 68, 5157
36. álvarez-Bercedo, P.; Martin, R. J. Am. Chem. Soc. 2010, 132, 17352
37. Tobisu, M.; Yamakawa, K.; Shimasaki, T.; Chatani, N. Chem. Commun. 2011, 47, 2946
38. Sergeev, A. G.; Hartwig, J. F. Science 2011, 332, 439
39. Cornella, J.; Gómez-Bengoa, E.; Martin, R. J. Am. Chem. Soc. 2013, 135, 1997
40. Diederich, F.; Stang, P. J.; Tykwinski, R. R., Eds. Acetylene Chemistry; Wiley-VCH: Weinheim, 2005. A themed issue on click chemistry
41. Finn, M. G.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1231 and articles therein
42. Zhang, W.; Moore, J. S. Adv. Synth. Catal. 2007, 349, 93
43. A review on recent advances in nickel catalysis: Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299
44. Streitwieser, A., Jr.; Scannon, P. J.; Niemeyer, H. M. J. Am. Chem. Soc. 1972, 94, 7936
45. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456
46. Tsukada, N.; Ninomiya, S.; Aoyama, Y.; Inoue, Y. Org. Lett. 2007, 9, 2919
47. Nishimura, T.; Guo, X.-X.; Uchiyama, N.; Katoh, T.; Hayashi, T. J. Am. Chem. Soc. 2008, 130, 1576
48. Shirakura, M.; Suginome, M. J. Am. Chem. Soc. 2008, 130, 5410
49. Ogata, K.; Murayama, H.; Sugasawa, J.; Suzuki, N.; Fukuzawa, S.-i. J. Am. Chem. Soc. 2009, 131, 3176
50. Nicolai, S.; Erard, S.; González, D. F.; Waser, J. Org. Lett. 2010, 12, 384
51. Brand, J. P.; Charpentier, J.; Waser, J. Angew. Chem., Int. Ed. 2009, 48, 9346
52. Ogata, K.; Sugasawa, J.; Fukuzawa, S.-i. Angew. Chem., Int. Ed. 2009, 48, 6078
53. Tobisu, M.; Ano, Y.; Chatani, N. Org. Lett. 2009, 11, 3250
54. Brand, J. P.; Waser, J. Angew. Chem., Int. Ed. 2010, 49, 7304
55. Ogata, K.; Atsuumi, Y.; Fukuzawa, S.-i. Org. Lett. 2011, 13, 122
56. Nicolai, S.; Piemontesi, C.; Waser, J. Angew. Chem., Int. Ed. 2011, 50, 4680
57. Ano, Y.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 12984
58. Shibata, Y.; Tanaka, K. Angew. Chem., Int. Ed. 2011, 50, 10917
59. Ano, Y.; Tobisu, M.; Chatani, N. Org. Lett. 2011, 14, 354
60. Ano, Y.; Tobisu, M.; Chatani, N. Synlett 2012, 23, 2763
61. Li, Y.; Brand, J. P.; Waser, J. Angew. Chem., Int. Ed. 2013, 52, 6743
62. Torrens, H. Coord. Chem. Rev. 2005, 249, 1957
63. Amii, H.; Uneyama, K. Chem. Rev. 2009, 109, 2119
64. Sun, A. D.; Love, J. A. Dalton Trans. 2010, 39, 10362
65. Nakao, Y.; Hiyama, T. Pure Appl. Chem. 2008, 80, 1097
66. Tobisu, M.; Chatani, N. Chem. Soc. Rev. 2008, 37, 300
67. Nakao, Y. Bull. Chem. Soc. Jpn. 2012, 85, 731
68. Wang, R.; Falck, J. R. RSC Adv. 2014, 4, 1062
69. Alkynylation of highly activated 2-nitrofluroarenes is known: Cargill, M. R.; Sandford, G.; Kilickiran, P.; Nelles, G. Tetrahedron 2013, 69, 512
70. Penney, J. M.; Miller, J. A. Tetrahedron Lett. 2004, 45, 4989
71. Yao, T.; Campo, M. A.; Larock, R. C. J. Org. Chem. 2005, 70, 3511
72. Wang, K.; Lü, M.; Yu, A.; Zhu, X.; Wang, Q. J. Org. Chem. 2009, 74, 935
73. Li, C.-W.; Wang, C.-I.; Liao, H.-Y.; Chaudhuri, R.; Liu, R.-S. J. Org. Chem. 2007, 72, 9203
74. Shimizu, M.; Nagao, I.; Tomioka, Y.; Hiyama, T. Angew. Chem., Int. Ed. 2008, 47, 8096
75. Tsuji, H.; Ueda, Y.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2010, 132, 11854
76. Mochida, K.; Kawasumi, K.; Segawa, Y.; Itami, K. J. Am. Chem. Soc. 2011, 133, 10716