Copper/silver-mediated direct ortho-ethynylation of unactivated (hetero)aryl C-H bonds with terminal alkyne

Chemistry - A European Journal

Volumn 21, Issue 1, 2015, Pages 205-209

  Liu, Yue Jin ^a   Liu, Yan Hua ^a   Yin, Xue Song ^a   Gu, Wen Jia ^a   Shi, Bing Feng ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Alkynylation; C H activation; Copper; Crosscoupling; Directing groups

Indexed keywords

ACTIVATION ANALYSIS; CATALYSTS; COPPER; FUNCTIONAL GROUPS; HYDROCARBONS; SYNTHESIS (CHEMICAL);

ALKYNYLATIONS; C-H ACTIVATION; C-H FUNCTIONALIZATION; COPPER CATALYST; CROSS-COUPLINGS; DIRECTING GROUPS; EFFICIENT SYNTHESIS; TERMINAL ALKYNE;

C (PROGRAMMING LANGUAGE);

ALKYNES; CARBON; COPPER; HETEROCYCLIC COMPOUNDS; HYDROGEN; SILVER;

CHEMISTRY; KINETICS; OXIDATION-REDUCTION;

ALKYNES; CARBON; COPPER; HETEROCYCLIC COMPOUNDS; HYDROGEN; KINETICS; OXIDATION-REDUCTION; SILVER;

EID: 84920444920     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201405594     Document Type: Article

References (99)

1. a) Acetylene Chemistry: Chemistry, Biology and Material Science (Eds.: F. Diederich, P. J. Stang, R. R. Tykwinski), Wiley-VCH, Weinheim, 2005;
2. b) S. Toyota, Chem. Rev. 2010, 110, 5398-5424.
3. a) K. J. Sonogashira, Organomet. Chem. 2002, 653, 46-49;
4. b) R. R. Tykwinski, Angew. Chem. Int. Ed. 2003, 42, 1566-1568;
5. Angew. Chem. 2003, 115, 1604-1606;
6. c) H. Plenio, Angew. Chem. Int. Ed. 2008, 47, 6954-6956;
7. Angew. Chem. 2008, 120, 7060-7063;
8. d) R. Chinchilla, C. Nájera, Chem. Soc. Rev. 2011, 40, 5084-5121.
9. A. S. Dudnik, V. Gevorgyan, Angew. Chem. Int. Ed. 2010, 49, 2096-2098;
10. Angew. Chem. 2010, 122, 2140-2142.
11. a) Y.-H. Xu, Q.-C. Zhang, T. He, F.-F. Meng, T.-P. Loh, Adv. Synth. Catal. 2014, 356, 1539-1543;
12. b) J. He, M. Wasa, K. S. L. Chan, J. Q. Yu, J. Am. Chem. Soc. 2013, 135, 3387-3390;
13. c) Y. Ano, M. Tobisu, N. Chatani, Org. Lett. 2012, 14, 354-357;
14. d) Y. Ano, M. Tobisu, N. Chatani, Synlett 2012, 2763-2767;
15. e) Y. Ano, M. Tobisu, N. Chatani, J. Am. Chem. Soc. 2011, 133, 12984-12986;
16. f) M. Tobisu, Y. Ano, N. Chatani, Org. Lett. 2009, 11, 3250-3252;
17. g) S. H. Kim, S. Chang, Org. Lett. 2010, 12, 1868-1871;
18. h) N. Matsuyama, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 4156-4159;
19. i) F. Besselièvre, S. Piguel, Angew. Chem. Int. Ed. 2009, 48, 9553-9556;
20. Angew. Chem. 2009, 121, 9717-9720;
21. j) I. V. Seregin, V. Ryabova, V. Gevorgyan, J. Am. Chem. Soc. 2007, 129, 7742-7743;
22. k) K. Kobayashi, M. Arisawa, M. Yamaguchi, J. Am. Chem. Soc. 2002, 124, 8528-8529.
23. a) F. Xie, Z. Qi, S. Yu, X. Li, J. Am. Chem. Soc. 2014, 136, 4780-4787;
24. b) C. Feng, T.-P. Loh, Angew. Chem. Int. Ed. 2014, 53, 2722-2726;
25. c) Y. Li, J. P. Brand, J. Waser, Angew. Chem. Int. Ed. 2013, 52, 6743-6747;
26. Angew. Chem. 2013, 125, 6875-6879;
27. d) J. P. Brand, J. Waser, Angew. Chem. Int. Ed. 2010, 49, 7304-7307;
28. Angew. Chem. 2010, 122, 7462-7465;
29. For a review, see: e) J. P. Brand, J. Waser, Chem. Soc. Rev. 2012, 41, 4165-4179.
30. a) Y. Wei, H. Zhao, J. Kan, W. Su, M. Hong, J. Am. Chem. Soc. 2010, 132, 2522-2523;
31. b) N. Matsuyama, M. Kitahara, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2010, 12, 2358-2361;
32. c) M. Kitahara, K. Hirano, H. Tsurugi, T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 1772-1775;
33. d) S. H. Kim, J. Yoon, S. Chang, Org. Lett. 2011, 13, 1474-1477;
34. e) F. Shibahara, Y. Dohke, T. Murai, J. Org. Chem. 2012, 77, 5381;
35. f) S. Ding, Y. Yan, N. Jiao, Chem. Commun. 2013, 49, 4250-4252.
36. a) T. Haro, C. Nevado, J. Am. Chem. Soc. 2010, 132, 1512-1513;
37. b) L. Yang, L. Zhao, C.-J. Li, Chem. Commun. 2010, 46, 4184-4186;
38. c) X. Jie, Y. Shang, P. Hu, W. Su, Angew. Chem. Int. Ed. 2013, 52, 3630-3633;
39. Shang, P. Hu, W. Su, Angew. Chem. Int. Ed. 2013, 52, 3630-3633;
40. Angew. Chem. 2013, 125, 3718-3721.
41. S. H. Kim, S. H. Park, S. Chang, Tetrahedron 2012, 68, 5162-5166.
42. A copper-mediated oxidative alkynylation and annulations of arenes was reported recently: J. Dong, F. Wang, J. You, Org. Lett. 2014, 16, 2884-2887.
43. During the submission of this manuscript, a highly related coppermediated C-H alkynylation of (hetero)arenes with terminal alkynes using a different oxazoline-type directing group was reported, see: M. Shang, H.-L. Wang, S.-Z. Sun, H.-X. Dai, J.-Q. Yu, J. Am. Chem. Soc. 2014, 136, 11590.
44. X. Chen, X.-S. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 6790-6791.
45. For selected reviews, see: a) C. Zhang, C. Tang, N. Jiao, Chem. Soc. Rev. 2012, 41, 3464-3484;
46. b) A. E.; King, L. M. Huffman, A. Casitas, M. Costas, X. Ribas, S. S. Stahl, J. Am. Chem. Soc. 2010, 132, 12068-12073
47. Wendlandt, A. M. Suess, S. S. Stahl, Angew. Chem. Int. Ed. 2011, 50, 11062-11087;
48. Angew. Chem. 2011, 123, 11256-11283;
49. c) O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074-1086.
50. For selected examples, see: a) T. Uemura, S. Imoto, N. Chatani, Chem. Lett. 2006, 35, 842-843;
51. b) G. Brasche, S. L. Buchwald, Angew. Chem. Int. Ed. 2008, 47, 1932-1934;
52. Angew. Chem. 2008, 120, 1958-1960;
53. c) S. Ueda, H. Nagasawa, Angew. Chem. Int. Ed. 2008, 47, 6411-6413;
54. Angew. Chem. 2008, 120, 6511-6513;
55. d) R. J. Phipps, N. P. Grimster, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 8172;
56. e) H. Zhao, M. Wang, W. Su, M. Hong, Adv. Synth. Catal. 2010, 352, 1301-1306;
57. f) H. Wang, Y. Wang, C. Peng, J. Zhang, Q. Zhu, J. Am. Chem. Soc. 2010, 132, 13217-13219;
58. g) B.-X. Tang, R.-J. Song, C.-Y. Wu, Y. Liu, M.-B. Zhou, W.-T. Wei, G.-B. Deng, D.-L. Yin, J.-H. Li, J. Am. Chem. Soc. 2010, 132, 8900-8902;
59. h) M. Kitahara, N. Umeda, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc. 2011, 133, 2160-2162;
60. i) Q. Liu, P. Wu, Y. Yang, Z. Zeng, J. Liu, H. Yi, A. Lei, Angew. Chem. Int. Ed. 2012, 51, 4666-4670;
61. Angew. Chem. 2012, 124, 4744-4748;
62. j) J. Gallardo-Donaire, R. Martin, J. Am. Chem. Soc. 2013, 135, 9350-9353;
63. k) S. Bhadra, C. Matheis, D. Katayev, L. J. Gooben, Angew. Chem. Int. Ed. 2013, 52, 9279-9283;
64. Angew. Chem. 2013, 125, 9449-9453.
65. For pioneer work of the use of bidentate auxiliary, see: a) V. G. Zaitsev, D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 13154-13155;
66. b) D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2010, 132, 3965-3972.
67. For reviews and selected examples on transition-metal-catalyzed C-H functionalization directed by bidentate auxiliary, see: a) G. Rouquet, N. Chatani, Angew. Chem. Int. Ed. 2013, 52, 11726-11734;
68. Angew. Chem. 2013, 125, 11942-11959;
69. b) C. Gu, H. H. Al Mamari, K. Graczyk, E. Diers, L. Ackermann, Angew. Chem. Int. Ed. 2014, 53, 3868-3871;
70. c) Y. Aihara, N. Chatani, J. Am. Chem. Soc. 2014, 136, 898-901;
71. d) C. P. Ting, T. J. Maimone, Angew. Chem. Int. Ed. 2014, 53, 3115-3119;
72. e) R. Shang, L. Ilies, A. Matsumoto, E. Nakamura, J. Am. Chem. Soc. 2013, 135, 6030-6032;
73. f) S.-Y. Zhang, G. He, W. A. Nack, Y. Zhao, Q. Li, G. Chen, J. Am. Chem. Soc. 2013, 135, 2124-2127;
74. g) G. He, G. Chen, Angew. Chem. Int. Ed. 2011, 50, 5192-5196;
75. Angew. Chem. 2011, 123, 5298-5302.
76. For examples of Cu-mediated C-H functionalization directed by bidentate auxiliary, see: a) L. D. Tran, I. Popov, O. Daugulis, J. Am. Chem. Soc. 2012, 134, 18237-18240;
77. b) T. Truong, K. Klimovica, O. Daugulis, J. Am. Chem. Soc. 2013, 135, 9342-9345;
78. c) J. Roane, O. Daugulis, Org. Lett. 2013, 15, 5842;
79. d) M. Nishino, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 2013, 52, 4457-4461;
80. Angew. Chem. 2013, 125, 4553-4557;
81. e) A. M. Suess, M. Z. Ertem, C. J. Cramer, S. S. Stahl, J. Am. Chem. Soc. 2013, 135, 9797-9804;
82. f) B. Urones, Á. M. Martínez, N. Rodríguez, R. G. Arrayás, J. Carretero, Chem. Commun. 2013, 49, 11044;
83. g) Z. Wang, J.-Z. Ni, Y. Kuninobu, M. Kanai, Angew. Chem. Int. Ed. 2014, 53, 3496-3499;
84. h) X. Wu, Y. Zhao, G. Zhang, H. Ge, Angew. Chem. Int. Ed. 2014, 53, 3706-3710;
85. i) Q. Li, S.-Y. Zhang, G. He, Z. Ai, W. A. Nack, G. Chen, Org. Lett. 2014, 16, 1764-1767;
86. j) M. Shang, S.-Z. Sun, H.-X. Dai, J.-Q. Yu, J. Am. Chem. Soc. 2014, 136, 3354-3357.
87. a) F.-J. Chen, S. Zhao, F. Hu, K. Chen, Q. Zhang, S.-Q. Zhang, B.-F. Shi, Chem. Sci. 2013, 4, 4187-4192;
88. b) Q. Zhang, K. Chen, W.-H. Rao, Y.-J. Zhang, F.-J. Chen, B.-F. Shi, Angew. Chem. Int. Ed. 2013, 52, 13588-13592;
89. Angew. Chem. 2013, 125, 13833-13837;
90. c) Q. Zhang, X.-S. Yin, S. Zhao, S.-L. Fang, B.-F. Shi, Chem. Commun. 2014, 50, 8353-8355;
91. d) X. Li, Y.-H. Liu, W.-J. Gu, B. Li, F.-J. Chen, B.-F. Shi, Org. Lett. 2014, 16, 3904-3907.
92. For selected examples, see: a) D. Ma, F. Liu, Chem. Commun. 2004, 1934-1935;
93. b) J.-H. Li, J.-L. Li, D.-P. Wang, S.-F. Pi, Y.-X. Xie, M.-B. Zhang, X.-C. Hu, J. Org. Chem. 2007, 72, 2053-2057;
94. c) E. Zuidema, C. Bolm, Chem. Eur. J. 2010, 16, 4181-4185.
95. a) Z.-L. Wang, L. Zhao, M.-X. Wang, Org. Lett. 2012, 14, 1472-1475;
96. b) Z.-L. Wang, L. Zhao, M.-X. Wang, Org. Lett. 2011, 13, 6560-6563;
97. c) A. E.; King, L. M. Huffman, A. Casitas, M. Costas, X. Ribas, S. S. Stahl, J. Am. Chem. Soc. 2010, 132, 12068-12073;
98. d) L. M. Huffman, S. S. Stahl, J. Am. Chem. Soc. 2008, 130, 9196-9197.
99. CCDC 1011982 (5 f) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.