SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2015 , Vol. 35 >Issue 3: 570 - 577

DOI: https://doi.org/10.6023/cjoc201412048

REVIEW

Transition-Metal-Catalyzed C—H Alkynylation

  • Wang Mingming ,
  • Wang Zixiao ,
  • Shang Ming ,
  • Dai Huixiong
Expand
  • a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
    b Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444

Received date: 2014-12-29

  Revised date: 2015-01-26

  Online published: 2015-01-28

Supported by

Project supported by the National Natural Science Foundation of China (No. 21472211).

Fold

Abstract

Alkynyl compounds are paramount skeletons in pharmaceuticals and natural products, and great importance has been attached to its synthesis by organic chemists. Recently, transition-metal-catalyzed C—H alkynylation has attracted tremendous interest as a valuable tool for construction of alkynyl compounds. This review gives a summary of progress having been made in the field of the C(sp2)—H and C(sp3)—H alkynylation over the last ten years.

Key words： alkynylation; C—H activation; alkyne; cross dehydrogen coupling

Cite this article

Wang Mingming , Wang Zixiao , Shang Ming , Dai Huixiong . Transition-Metal-Catalyzed C—H Alkynylation[J]. Chinese Journal of Organic Chemistry, 2015 , 35(3) : 570 -577 . DOI: 10.6023/cjoc201412048

References

[1] Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
[2] Dudnik, A. S.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 2096.
[3] Kobayashi, K.; Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2002, 124, 8528.
[4] Amemiya, R.; Fujii, A.; Yamaguchi, M. Tetrahedron Lett. 2004, 45, 4333.
[5] Tobisu, M.; Ano, Y.; Chatani, N. Org. Lett. 2009, 11, 3250.
[6] Kalinin, V. K.; Pashchenko, D. N.; She, F. M.; Mendeleev. Commun. 1992, 2, 60.
[7] Trofimov, B. A.; Stepanova, Z. V.; Sobenina, L. N.; Mikhaleva, A. B. I.; Ushakov, I. A. Tetrahedron Lett. 2004, 45, 6513.
[8] (a) Sobenina, L. N.; Demenev, A. P.; Mikhaleva, A. b. I.; Ushakov, I. A.; Vasil'tsov, A. M.; Ivanov, A. V.; Trofimov, B. A. Tetrahedron Lett. 2006, 47, 7139. (b) Gu, Y.; Wang, X.-M. Tetrahedron Lett. 2009, 50, 763.
[9] Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.
[10] (a) Matsuyama, N.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2009, 11, 4156. (b) Besselievre, F.; Piguel, S. Angew. Chem., Int. Ed. 2009, 48, 9553. (c) Kim, S. H.; Chang, S. Org. Lett. 2010, 12, 1868.
[11] Kawano, T.; Matsuyama, N.; Hirano, K.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2010, 75, 1764.
[12] Chatani, N.; Tobisu, M.; Ano, Y. Synlett 2012, 23, 2763.
[13] Ano, Y.; Tobisu, M.; Chatani, N. Org. Lett. 2012, 14, 354.
[14] Xu, Y.-H.; Zhang, Q.-C.; He, T.; Meng, F.-F.; Loh, T.-P. Adv. Synth. Catal. 2014, 356, 1539.
[15] Brand, J. P.; Charpentier, J.; Waser, J. Angew. Chem., Int. Ed. 2009, 48, 9346.
[16] Tolnai, G. L.; Ganss, S.; Brand, J. P.; Waser, J. Org. Lett. 2013, 15, 112.
[17] Brand, J. P.; Waser, J. Angew. Chem., Int. Ed. 2010, 49, 7304.
[18] Koller, R.; Stanek, K.; Stolz, D.; Aardoom, R.; Niedermann, K.; Togni, A. Angew. Chem., Int. Ed. 2009, 48, 4332.
[19] Brand, J. P.; Waser, J. Org. Lett. 2012, 14, 744.
[20] Li, Y.; Waser, J. Beilstein J. Org. Chem. 2013, 9, 1763.
[21] Feng, C.; Loh, T. P. Angew. Chem., Int. Ed. 2014, 53, 2722.
[22] (a) Xie, F.; Qi, Z.; Yu, S.; Li, X. J. Am. Chem. Soc. 2014, 136, 4780. (b) Zhang, X.; Qi, Z.; Gao, J.; Li, X. Org. Biomol. Chem. 2014, 12, 9329.
[23] Wu, Y.; Yang, Y.; Zhou, B.; Li, Y. J. Org. Chem. 2015, 80, 1946.
[24] Collins, K. D.; Lied, F.; Glorius, F. Chem. Commun. 2014, 50, 4459.
[25] Feng, C.; Feng, D.; Loh, T.-P. Chem. Commun. 2014, 50, 9865.
[26] Feng, C.; Feng, D.; Luo, Y.; Loh, T. P. Org. Lett. 2014, 16, 5956.
[27] Matsuyama, N.; Kitahara, M.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 2358.
[28] Wei, Y.; Zhao, H.; Kan, J.; Su, W.; Hong, M. J. Am. Chem. Soc. 2010, 132, 2522.
[29] Haro, T.; Nevado, C. J. Am. Chem. Soc. 2010, 132, 1512.
[30] Kawano, T.; Matsuyama, N.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2010, 75, 1764.
[31] Yang, L.; Zhao, L.; Li, C.-J. Chem. Commun. 2010, 46, 4184.
[32] Kim, S. H.; Yoon, J.; Chang, S. Org. Lett. 2011, 13, 1474.
[33] Jie, X.; Shang, Y.; Hu, P.; Su, W. Angew. Chem., Int. Ed. 2013, 52, 3630.
[34] Weng, Y.; Cheng, B.; He, C.; Lei, A. Angew. Chem., Int. Ed. 2012, 51, 9547.
[35] Kim, S. H.; Park, S. H.; Chang, S. Tetrahedron 2012, 68, 5162.
[36] Shang, M.; Wang, H.-L.; Sun, S.-Z.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 11590.
[37] Liu, Y.-J.; Liu, Y.-H.; Yin, X.-S.; Gu, W.-J.; Shi, B.-F. Chem. Eur. J. 2015, 21, 205.
[38] Ano, Y.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 12984.
[39] Al-Amin, M.; Arisawa, M.; Shuto, S.; Ano, Y.; Tobisu, M.; Chatani, N. Adv. Synth. Catal. 2014, 356, 1631.
[40] He, J.; Wasa, M.; Chan, K. S.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 3387.

Options
Outlines

/

〈 〉