Ni(II)-catalyzed dehydrative alkynylation of unactivated (hetero)aryl C-H bonds using oxygen: A user-friendly approach

Chemical Communications

Volumn 51, Issue 58, 2015, Pages 11650-11653

  Liu, Yan Hua ^a   Liu, Yue Jin ^a   Yan, Sheng Yi ^a   Shi, Bing Feng ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; CARBON; HYDROGEN; NICKEL; OXIDIZING AGENT; OXYGEN; ALKYNE;

ALKYNYLATION; ANNULATION REACTION; ARTICLE; ATMOSPHERIC PRESSURE; CATALYSIS; CATALYST; CHEMICAL REACTION; COVALENT BOND; SYNTHESIS; CHEMISTRY;

ALKYNES; ATMOSPHERIC PRESSURE; CATALYSIS; NICKEL; OXIDANTS; OXYGEN;

EID: 84936166046     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c5cc03729h     Document Type: Article

References (81)

1. F. Diederich, P. J. Stang and R. R. Tykwinski, Acetylene Chemistry: Chemistry, Biology and Material Science, Wiley-VCH, Weinheim, 2005
2. L. Anastasia E. Negishi Chem. Rev. 2003 103 1979
3. F. Alonso I. P. Beletskaya M. Yus Chem. Rev. 2004 104 3079
4. C. Liu H. Zhang W. Shi A.-W. Lei Chem. Rev. 2011 111 1780
5. J. P. Brand J. Waser Chem. Soc. Rev. 2012 41 4165
6. B. Godoi R. F. Schumacher G. Zeni Chem. Rev. 2011 111 2937
7. R. Chinchilla C. Nájera Chem. Rev. 2014 114 1783
8. K. Sonogashira J. Organomet. Chem. 2002 653 46
9. R. Chinchilla C. Nájera Chem. Rev. 2007 107 874
10. H. Doucet J. Cyrille Hierso Angew. Chem., Int. Ed. 2007 46 834
11. Z. Shao F. Peng Angew. Chem., Int. Ed. 2010 49 9566
12. A. S. Dudnik V. Gevorgyan Angew. Chem., Int. Ed. 2010 49 2096
13. J. P. Brand J. Waser Chem. Soc. Rev. 2012 41 4165
14. Y.-J. Liu Y.-H. Liu S.-Y. Yan B.-F. Shi Chem. Commun. 2015 51 6388
15. F. Xie Z.-S. Qi S.-J. Yu X.-W. Li J. Am. Chem. Soc. 2014 136 4780
16. C. Feng T.-P. Loh Angew. Chem., Int. Ed. 2014 53 2722
17. C. Feng D. Feng T.-P. Loh Chem. Commun. 2014 50 9865
18. G. L. Tolnai S. Ganss J. P. Brand J. Waser Org. Lett. 2013 15 112
19. Y. Ano M. Tobisu N. Chatani Org. Lett. 2012 14 354
20. J. P. Brand J. Waser Org. Lett. 2012 14 744
21. T. Kawano N. Matsuyama K. Hirano T. Satoh M. Miura J. Org. Chem. 2010 75 1764
22. N. Matsuyama K. Hirano T. Satoh M. Miura Org. Lett. 2009 11 4156
23. M. Tobisu Y. Ano N. Chatani Org. Lett. 2009 11 3250
24. J. P. Brand J. Charpentier J. Waser Angew. Chem., Int. Ed. 2009 48 9346
25. I. V. Seregin V. Ryabova V. Gevorgyan J. Am. Chem. Soc. 2007 129 7742
26. S. A. Girard T. Knauber C.-J. Li Angew. Chem., Int. Ed. 2014 53 74
27. F. Jia Z. Li Org. Chem. Front. 2014 1 194
28. C. Zhang C. Tang N. Jiao Chem. Soc. Rev. 2012 41 3464
29. L. Yang H. Huang Catal. Sci. Technol. 2012 2 1099
30. C. S. Yeung V. M. Dong Chem. Rev. 2011 111 1215
31. C.-J. Li Acc. Chem. Res. 2009 42 335
32. Z. Li C.-J. Li J. Am. Chem. Soc. 2004 126 11810
33. Z. Li C.-J. Li Org. Lett. 2004 6 4997
34. M. Chen X. Zheng W. Li J. He A. Lei J. Am. Chem. Soc. 2010 132 4101
35. C. He S. Guo J. Ke J. Hao H. Chen A. Lei J. Am. Chem. Soc. 2012 134 5766
36. J. Ke C. He H. Liu M. Li A. Lei Chem. Commun. 2013 49 7549
37. M. Gao C. He H. Chen R. Bai B. Cheng A. Lei Angew. Chem., Int. Ed. 2013 52 6958
38. T. de-Haro C. Nevado J. Am. Chem. Soc. 2010 132 1512
39. Y. Wei H.-Q. Zhao J. Kan W.-P. Su M.-C. Hong J. Am. Chem. Soc. 2010 132 2522
40. M. Kitahara K. Hirano H. Tsurug i T. Satoh M. Miura Chem.-Eur. J. 2010 16 1772
41. L. Yang L. Zhao C.-J. Li Chem. Commun. 2010 46 4184
42. S. H. Kim J. Yoon S. Chang Org. Lett. 2011 13 1474
43. F. Shibahara Y. Dohke T. Murai J. Org. Chem. 2012 77 5381
44. S. H. Kim S. H. Park S. Chang Tetrahedron 2012 68 5162
45. X.-M. Jie Y.-P. Shang P. Hu W.-P. Su Angew. Chem., Int. Ed. 2013 52 3630
46. N. Matsuyama M. Kitahara K. Hirano T. Satoh M. Miura Org. Lett. 2010 12 2358
47. M. Shang H.-L. Wang S.-Z. Sun H.-X. Dai J.-Q. Yu J. Am. Chem. Soc. 2014 136 11590
48. Y.-J. Liu Y.-H. Liu X.-S. Yin W.-J. Gu B.-F. Shi Chem.-Eur. J. 2015 21 205
49. G. Rouquet N. Chatani Angew. Chem., Int. Ed. 2013 52 11726
50. B. Zhang H.-X. Guan B. Liu B.-F. Shi Chin. J. Org. Chem. 2014 34 1487
51. O. Daugulis J. Roane L. D. Tran Acc. Chem. Res. 2015 48 1053
52. R. K. Rit M. R. Yadav K. Ghosh A. K. Sahoo Tetrahedron 2015 71 4450
53. V. G. Zaitsev D. Shabashov O. Daugulis J. Am. Chem. Soc. 2005 127 13154
54. F.-J. Chen S. Zhao F. Hu K. Chen Q. Zhang S.-Q. Zhang B.-F. Shi Chem. Sci. 2013 4 4187
55. Q. Zhang K. Chen W.-H. Rao Y.-J. Zhang F.-J. Chen B.-F. Shi Angew. Chem., Int. Ed. 2013 52 13588
56. Z. Shi C. Zhang C. Tang N. Jiao Chem. Soc. Rev. 2012 41 3381
57. A. N. Campbell S. S. Stahl Acc. Chem. Res. 2012 45 851
58. W.-Q. Wu H.-F. Jiang Acc. Chem. Res. 2012 45 1736
59. L. Jin A. Lei Sci. China: Chem. 2012 55 2027
60. T. Punniyamurthy S. Velusamy J. Iqbal Chem. Rev. 2005 105 2329
61. W. Yin C. He M. Chen H. Zhang A. Lei Org. Lett. 2009 11 709
62. G. Evano N. Blanchard M. Toumi Chem. Rev. 2008 108 3054
63. S. Ding Y. Yan N. Jiao Chem. Commun. 2013 49 4250
64. J. Dong F. Wang J. You Org. Lett. 2014 16 2884
65. J. He M. Wasa K. S. L. Chan J.-Q. Yu J. Am. Chem. Soc. 2013 135 3387
66. S. Nicolai S. Erard D. F. González J. Waser Org. Lett. 2010 12 384
67. S. Nicolai C. Piemontesi J. Waser Angew. Chem., Int. Ed. 2011 50 4680
68. Y.-J. Liu Z.-Z. Zhang S.-Y. Yan Y.-H. Liu B.-F. Shi Chem. Commun. 2015 51 7899
69. S.-Y. Yan Y.-J. Liu B. Liu Y.-H. Liu Z.-Z. Zhang B.-F. Shi Chem. Commun. 2015 51 7341
70. S.-Y. Yan Y.-J. Liu B. Liu Y.-H. Liu Z.-Z. Zhang B.-F. Shi Chem. Commun. 2015 51 4069
71. C. Lin D.-Y. Li B.-J. Wang J.-Z. Yao Y. H. Zhang Org. Lett. 2015 17 1328
72. X. Wang R.-H. Qiu C.-Y. Yan V. P. Reddy L.-Z. Zhu X.-H. Xu S.-F. Yin Org. Lett. 2015 17 1970
73. X.-H. Ye J. L. Petersen X.-D. Shi Chem. Commun. 2015 51 7863
74. Y. Aihara M. Tobisu Y. Fukumoto N. Chatani J. Am. Chem. Soc. 2014 136 15509
75. H. Shiota Y. Ano Y. Aihara Y. Fukumoto N. Chatani J. Am. Chem. Soc. 2011 133 14952
76. Y. Aihara N. Chatani J. Am. Chem. Soc. 2013 135 5308
77. W.-F. Song S. Lackner L. Ackermann Angew. Chem., Int. Ed. 2014 53 1
78. X.-S. Wu Y. Zhao H.-B. Ge J. Am. Chem. Soc. 2014 136 1789
79. Y. Aihara N. Chatani J. Am. Chem. Soc. 2014 136 898
80. L. C. M. Castro N. Chatani Chem. Lett. 2015 44 410
81. C. Theunissen G. Evano Org. Lett. 2014 16 4488