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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 08: 1628 - 1646

DOI: https://doi.org/10.6023/cjoc201211039

Reviews

Recent Progress in Copper Catalyzed C—H Functionalizations

  • Yu Haizhu ,
  • Su Shengqin ,
  • Zhang Chi ,
  • Dang Zhi-Min
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  • Department of Polymer Science and Engineering, University of Science and Technology Beijing, Beijing 100083

Received date: 2012-11-21

  Revised date: 2013-02-18

  Online published: 2013-03-14

Supported by

Project supported by the National Natural Science Foundation of China (No. 21202006) and the Fundamental Research Funds for the Central Universities (No. FRF-TP-13-023A).

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Abstract

The past decades have witnessed the great progress of copper-catalyzed C—H functionalization reactions, which have shown great potential in synthesizing multi-functionalized organic compounds. In the present review, the recent development of Cu(I)/Cu(II) catalyzed sp, sp2 and sp3 C—H bond functionalizations since 2008 is systematically summarized. Besides of the reaction conditions and substrate scopes for different C—H functionalizations, and the reported mechanistic studies were also summarized and discussed.

Key words： Cu catalysis; C—H functionalization; cross coupling; mechanism

Cite this article

Yu Haizhu , Su Shengqin , Zhang Chi , Dang Zhi-Min . Recent Progress in Copper Catalyzed C—H Functionalizations[J]. Chinese Journal of Organic Chemistry, 2013 , 33(08) : 1628 -1646 . DOI: 10.6023/cjoc201211039

References

[1] For recent examples, please see:
(a) Yu, J.-Q.; Giri, R.; Chen, X. Org. Biomol. Chem. 2006, 4, 4041. (b) Li, B.; Tian, S.; Fang, Z.; Shi, Z. Angew. Chem., Int. Ed. 2008, 47, 1115.
(c) Li, J.-J.; Mei, T.-S.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 6452.
(d) Grimster, N. P.; Gauntlett, C.; Godfrey, C. M. R.; Gaunt, M. J. Angew. Chem., Int. Ed. 2005, 44, 3125.
(e) Xiao, B.; Fu, Y.; Xu, J.; Gong, T. J.; Dai, J. J.; Yi, J.; Liu, L. J. Am. Chem. Soc. 2010, 132, 468.
(f) Beck, E. M.; Grimster, N. P.; Hatley, R.; Gaunt, M. J. J. Am. Chem. Soc. 2006, 128, 2528.
(g) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759.
(h) Perutz, R. N.; Sabo-Etienne, S. Angew. Chem., Int. Ed. 2007, 46, 2578.
(i) Mei, T.-S.; Wang, X.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 10806.
(j) Thu, H.-Y.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048.
(k) Stokes, B. J.; Dong, H.; Leslie, B. E.; Pumphrey, A. L.; Driver, T. G. J. Am. Chem. Soc. 2007, 129, 7500.
(l) Gao, K.; Yoshikai, N. J. Am. Chem. Soc. 2011, 133, 400.
(m) Kakiuchi, F.; Kochi, T.; Mizushima, E.; Murai, S. J. Am. Chem. Soc. 2010, 132, 17741.
(n) Xiao, B.; Gong, T.-J.; Liu, Z.-J.; Liu, J.-H.; Luo, D.-F.; Xu, J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 9250.
(o) Tsuchikama, K.; Kasagawa, M.; Hashimoto, Y.-K.; Endo, K.; Shibata, T. J. Org. Chem. 2008, 693, 3939.
(p) Xiao, B.; Gong, T. J.; Xu, J.; Liu, Z.-J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 1466;
(q) Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 5332.
(r) Wang, Y.; Cheng, G.; Cui, L. Chin. J. Org. Chem. 2012, 32, 2018 (in Chinese).
(王勇, 程国林, 崔秀灵, 有机化学, 2012, 32, 2018.)
(s) Li, D.; He, C.; Cai, H.; Wang, G. Chin. J. Org. Chem. 2013, 33, 203 (in Chinese).
(李丹丹, 何程林, 蔡海婷, 王官武, 有机化学, 2013, 33, 203.)
[2] Recent examples for other types of copper catalyzed C—C bond formation reactions, please see:
(a) Li, Z.; Bohle, D. S.; Li, C. J. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 8928.
(b) Chen, X.; Hao, X. S.; Goodhue, C. E.; Yu. J. Q. J. Am. Chem. Soc. 2006, 128, 6790.
(c) Uemura, T.; Imoto, S.; Chatani, N. Chem. Lett. 2006, 35, 842.
(d) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 6968.
(e) Zeng, W.; Chemler, S. R. J. Am. Chem. Soc. 2007, 129, 12948.
(f) Sherman, E. S.; Fuller, P. H.; Kasi, D.; Chemler, S. R. J. Org. Chem. 2007, 72, 3896.
(g) Fuller, P. H.; Chemler, S. R. Org. Lett. 2007, 9, 5477.
(h) Yang, C.-T.; Zhang, Z.-Q.; Liang, J.; Liu, J.-H.; Lu, X.-Y.; Chen, H.-H.; Liu, L. J. Am. Chem. Soc. 2012, 134, 11124.
(i) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941.
(j) Kohmura, Y.; Katsuki, T. Synlett 1999, 1231.
(k) Shuai, Q.; Deng, G.; Chua, Z.; Bohle, D. S.; Li, C.-J. Adv. Synth. Catal. 2010, 352, 632.
(l) Park, E. J.; Kim, S. H.; Chang, S. J. Am. Chem. Soc. 2008, 130, 17268.
(m) Xiong, T.; Li, Y.; Bi, X.; Lv, Y.; Zhang, Q. Angew. Chem., Int. Ed. 2011, 50, 7140.
(n) Yang, C.-T.; Zhang, Z.-Q.; Liu, Y.-C.; Liu, L. Angew. Chem, Int. Ed. 2011, 50, 3904.
(o) Bellina, F.; Rossi, S. Adv. Synth. Catal. 2010, 352, 1223.
(p) Moure, M. J.; SanMartin, R.; Dominguez, E. Angew. Chem., Int. Ed. 2012, 124, 3274.
(q) Yang, C.-T.; Fu, Y.; Huang, Y.-B.; Yi, J.; Guo, Q.-X.; Liu, L. Angew. Chem., Int. Ed. 2009, 48, 7398.
(r) Qin, Y.; Peng, Q.; Chin. J. Org. Chem. 2011, 31, 1169 (in Chinese).
(秦元成, 彭强, 有机化学, 2011, 31, 1169.)
(s) Liao, Q.; Xi, C. Chin. J. Org. Chem. 2012, 32, 986 (in Chinese).
(廖骞, 席婵娟, 有机化学, 2012, 32, 986.)
(t) Cui, P.; Liu, H.; Zhang, D.; Wang, C. Chin. J. Org. Chem. 2012, 32, 1401 (in Chinese).
(崔朋雷, 刘海燕, 张冬暖, 王春, 有机化学, 2012, 32, 1401.)
(t) Liu, W.; Bi, Y. Chin. J. Org. Chem. 2012, 32, 1041 (in Chinese).
(刘伟, 毕艳兰, 有机化学, 2012, 32, 1041.)
[3] Ljusberg, H.; Wahren, R. Acta Chem. Scand. 1973, 27, 2717.
[4] Wulfman, D. S.; Mcdaniel, R. S.; Peace, B. W. Tetrahedron Lett. 1976, 32, 1241.
[5] Tobisu, M.; Fujihara, H.; Koh, K.; Chatani, N. J. Org. Chem. 2010, 75, 4841.
[6] Guin, S.; Ghosh, T.; Rout, S. K.; Banerjee, A.; Patel, B. K. Org. Lett. 2011, 13, 5976.
[7] Ban, I.; Sudo, T.; Taniguchi, T.; Itami, K. Org. Lett. 2008, 10, 3607.
[8] Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
[9] (a) Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074.
(b) Kulkarni, A. A.; Daugulis, O. Synthesis 2009, 4087
[10] Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Angew. Chem., Int. Ed. 2011, 50, 11062.
[11] Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3464.
[12] Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 1128.
[13] Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.
[14] Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
[15] Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
[16] (a) Ljusberg, H.; Wahren, R. Acta Chem. Scand. 1973, 27, 2717.
(b) Shang, R.; Fu, Y.; Wang, Y.; Xu, Q.; Yu, H.-Z.; Liu, L. Angew. Chem., Int. Ed. 2009, 49, 9350.
[17] Yotphan, S.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2009, 11, 1511.
[18] Fan, S.; Chen, Z.; Zhang, X. Org. Lett. 2012, 14, 4950.
[19] Ye, S.; Liu, G.; Pu. S.; Wu, J. Org. Lett. 2012, 14, 70.
[20] Hwu, J. R.; Chuang, K.-S.; Chuang, S. H.; Tsay, S.-C. Org. Lett. 2005, 7, 1545.
[21] Feng, C.; Loh, T.-P. Chem. Sci. 2012, 3, 3458.
[22] (a) Parsons, A. T.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 9120.
(b) Wang, X.; Ye, Y.; Zhang, S.; Feng, J.; Xu, Y.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 16410.
(c) Xu, J.; Fu, Y.; Luo, D.-F.; Jiang, Y.-Y.; Xiao, B.; Liu, Z.-J.; Gong, T.-J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 15300.
(d) Pan, F.; Shi, Z. Acta Chim. Sinica 2012, 70, 1679 (in Chinese).
(潘菲, 施章杰, 化学学报, 2012, 70, 1679.)
(e) Lv, C.; Shen, Q.; Liu, D. Chin. J. Org. Chem. 2012, 32, 1380 (in Chinese).
(吕翠萍, 沈其龙, 刘丹, 有机化学, 2012, 32, 1380.)
(f) Qing, F. Chin. J. Org. Chem. 2012, 32, 815 (in Chinese).
(卿凤翎, 有机化学, 2012, 32, 815.)
[23] Besselievre, F.; Piguel, S.; Betzer, M. F.; Grierson, S. D. Org. Lett. 2008, 10, 4029.
[24] Axelrod, B.; Belzile, J. R. J. Org. Chem. 1958, 23, 919.
[25] Kawano, T.; Matsuyama, N.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2010, 75, 1764.
[26] Matsuyama, N.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2009, 11, 4156.
[27] (a) Zhao, D.; Wang, W.; Yang, F.; Lan, J.; Yang, L.; Gao, G.; You, J. Angew. Chem., Int. Ed. 2009, 48, 3296.
(b) Zhao, D.; Wang, W.; Yang, F.; Lan, J.; Yang, L.; Gao, G.; You, J. Angew. Chem., Int. Ed. 2009, 48, 4884.
[28] Huang, G.; Sun, H.; Qiu, X.; Jin, C.; Lin, C.; Shen, Y.; Jiang, J.; Wang, L. Org. Lett. 2011, 13, 5224.
[29] Hu, X. L. Chem. Sci. 2011, 2, 1867.
[30] Ren, P.; Salihu, I.; Scopelliti, R.; Hu, X. Org. Lett. 2012, 14, 1748.
[31] Ackermann, L.; Potukuchi, H. K.; Landsberg, D.; Vicente, R. Org. Lett. 2008, 10, 3081.
[32] Li, B.-J.; Tian, S.-L.; Fang, Z.; Shi, Z.-J. Angew. Chem., Int. Ed. 2008, 47, 1115.
[33] Tobisu, M.; Fujihara, H.; Koh, K.; Chatani, N. J. Org. Chem. 2010, 75, 4841.
[34] Liao, Q.; Zhang, L.; Li, S.; Xi, C. Org. Lett. 2011, 13, 228.
[35] Inomata, H.; Ogata, K.; Fukuzawa, S.-I.; Hou, Z. Org. Lett. 2012, 14, 3986.
[36] (a) Zhang, L.; Cheng, J.; Ohishi, T.; Hou, Z. Angew. Chem., Int. Ed. 2010, 49, 8670.
(b) Ariafard, A.; Zarkoob, F.; Batebi, H.; Stranger, R.; Yate, B. F. Organometallics 2011, 30, 6218.
[37] Tang, C.-H.; Jiao, N. J. Am. Chem. Soc. 2012, 134, 18924.
[38] Black, D. A.; Beveridge, R. E.; Arndtsen, B. A. J. Org. Chem. 2008, 73, 1906.
[39] Zhang, K.; Huang, Y.; Chen, R. Tetrahedron Lett. 2010, 51, 5463.
[40] Yang, F.; Li, J.; Xie, J.; Huang, Z.-Z. Org. Lett. 2010, 12, 5214.
[41] Wu, J.-C.; Song, R.-J.; Wang, Z.-Q.; Huang, X.-C.; Xie, Y.-X.; Li, J.-H. Angew. Chem., Int. Ed. 2012, 51, 3453.
[42] Fuentes, M. á.; Monge, M.; Olmos, M. E.; Rodríguez-Castillo, M.; Caballeroa, A. Inorg. Chim. Acta 2011, 369, 146.
[43] Morilla, M. E.; Díaz-Requejo, M. M.; Belderrain, Y. R.; Nicasio, M. C.; Trofimenko, S.; Pérez, P. J. Organometallics 2004, 23, 293.
[44] Fructos, R. M.; Belderrain, R. T.; Frémont, P.; Scott, M. N.; Nolan, P. S.; Díaz-Requejo, M. M.; Pérez, P. J. Angew. Chem., Int. Ed. 2005, 44, 5284.
[45] Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 8172.
[46] Phipps, R. J.; Gaunt, M. J. Science 2009, 323, 1593.
[47] Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046.
[48] Qin, Xu.-R.; Feng, B.-Y.; Dong, J.-X.; Li, X.-Y.; Yue, Y.; Lan, J.; You, J.-S. J. Org. Chem. 2012, 77, 7677
[49] Qu, G.-R.; Liang, L.; Niu, H.-Y.; Rao, W.-H.; Guo, H.-M.; Fossey, J. S. Org. Lett. 2012, 14, 4494.
[50] Ton, T. M. U.; Himawan, F.; Chang, J. W. W.; Chan, P. W. H. Chem.-Eur. J. 2012, 18, 12020.
[51] Kwong, H.-L.; Lee, W.-S. Tetrahedron: Asymmetry 2000, 11, 2299.
[52] Phipps, R. J.; McMurray, L.; Ritter, S.; Duong, H. A.; Gaunt, M. J. J. Am. Chem. Soc. 2012, 134, 10773.
[53] Moody, C. L.; Franckevičius, V.; Drouhin, P.; Klein, J. E. M. N.; Taylor, R. J. K. Tetrahedron Lett. 2012, 53, 1897.
[54] Bassleer, R.; Depauwgillet, M. C.; Massart, B.; Marnette, J. M.; Wiliquet, P.; Caprasse, M.; Angenot, L. Planta Med. 1982, 45, 123.
[55] (a) Jia, Y. X.; Kündig, E. P. Angew. Chem., Int. Ed. 2009, 48, 1636. (b) Perry, A.; Taylor, R. J. K. Chem. Commun. 2009, 3249.
[56] Jossang, A.; Jossang, P.; Hadi, H. A.; Sevenet, T.; Bodo, B. J. Org. Chem. 1991, 56, 6527.
[57] Posner, G. H. Org. React. 1975, 22, 253.
[58] (a) Wang, Z.-L.; Zhao, L.; Wang, M.-X. Org. Lett. 2012, 14, 1472. (b) Wang, Z.-L.; Zhan, L.; Wang, M.-X. Org. Lett. 2011, 13, 6560.
[59] Kawano, T.; Hirano, K.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2010, 132, 6900.
[60] Wang, Q.; Schreiber, S. L. Org. Lett. 2009, 11, 5178.
[61] Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2012, 134, 1298.
[62] Wang, X.; Jin, Y.; Zhao, Y. Zhao, Y.; Zhu, L.; Fu, H. Org. Lett. 2012, 14, 452.
[63] Ogura, H.; Takayanagi, H.; Yamazaki, Y.; Yonezawa, S.; Takagi, H.; Kobayashi, S.; Kamoshita, K. J. Med. Chem. 1972, 15, 923.
[64] Mitsuda, S.; Fujiwara, T.; Kimigafukuro, K.; Monguchi, D.; Mori, A. Tetrahedron Lett. 2012, 68, 3585.
[65] Ueda, S.; Nagasawa, H. Angew. Chem., Int. Ed. 2008, 47, 6411.
[66] (a) Viirre, R. D.; Evindar, G.; Batey, R. A. J. Org. Chem. 2008, 73, 3452.
(b) Evindar, G.; Batey, R. A. J. Org. Chem. 2006, 71, 1802.
[67] Cheung, C. W.; Buchwald, S. L. J. Org. Chem. 2012, 77, 7526.
[68] Guin, S.; Ghosh, T.; Rout, S. K.; Banerjee, A.; Patel, B. K. Org. Lett. 2011, 13, 5976.
[69] Kawano, T.; Yoshizumi, T.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2009, 11, 3072.
[70] He, G. S.; Tan, L.-S.; Zheng, Q.; Prasad, P. N. Chem. Rev. 2008, 108, 1245.
[71] (a) Guru, M. M.; Punniyamurthy, T. J. Org. Chem. 2012, 77, 5063. (b) Guru, M. M.; Ali, M. A.; Punniyamurthy, T. J. Org. Chem. 2011, 76, 5295.
[72] Tang, B.-X.; Song, R.-J.; Wu, C.-Y.; Liu, Y.; Zhou, M.-B.; Li, J.-H. J. Am. Chem. Soc. 2010, 132, 8900.
[73] Guru, M. M.; Ali, M. A.; Punniyamurthy, T. Org. Lett. 2011, 13, 1194.
[74] Lu, J.; Jin, Y.; Liu, H.; Jiang, Y.; Fu, H. Org. Lett. 2011, 13, 3694.
[75] Yang, L.; Lu, Z.; Stahl, S. S. Chem. Commun. 2009, 6460.
[76] (a) Zhang, S.-L.; Liu, L.; Fu, Y.; Guo, Q.-X. Organometallics 2007, 26, 4546.
(b) Yu, H.-Z.; Jiang, Y.-Y.; Fu, Y.; Liu, L. J. Am. Chem. Soc. 2010, 132, 18078.
(c) Jones, G. O.; Liu, P.; Houk, K. N.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 6205.
(d) Johnson, C. R.; Dutra, G. A. J. Am. Chem. Soc. 1973, 95, 7783.
(e) Kochi, J. K. J. Am. Chem. Soc. 1957, 79, 2942.
(f) Jenkins, C. L.; Kochi, J. K. J. Am. Chem. Soc. 1972, 94, 856.
(g) Jenkins, C. L.; Kochi, J. K. J. Am. Chem. Soc. 1972, 94, 843.
(h) Cohen, T.; Lewarchik, R. J.; Tarino, J. Z. J. Am. Chem. Soc. 1974, 96, 7753.
[77] Jones, G. O.; Liu, P.; Houk, K. N.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 6205.
[78] (a) Johnson, C. R.; Dutra, G. A. J. Am. Chem. Soc. 1973, 95, 7783.
(b) Kochi, J. K. J. Am. Chem. Soc. 1957, 79, 2942.
(c) Jenkins, C. L.; Kochi, J. K. J. Am. Chem. Soc. 1972, 94, 856.
(d) Cohen, T.; Lewarchik, R. J.; Tarino, J. Z. J. Am. Chem. Soc. 1974, 96, 7753.
[79] Wei, Y.; Zhao, H.; Kan, J. Su, W.; Hong, M. J. Am. Chem. Soc. 2010, 132, 2522.
[80] Xu, Z.; Yu, X.; Feng, X. Bao, M. J. Org. Chem. 2011, 76, 6901.
[81] Giles, R. L.; Nkansah, R. A.; Looper, R. E. J. Org. Chem. 2010, 75, 261.
[82] Rueping, M.; Tolstoluzhsky, N. Org. Lett. 2011, 13, 1095.
[83] Tolstoluzhsky, N.; Gorobets, N.; Kolos, N.; Desenko, S. J. Comb. Chem. 2008, 10, 893.
[84] Rueping, M.; Nachtsheim, B. J.; Scheidt, T. Org. Lett. 2006, 8, 3717.
[85] Thi, M. U. T.; Tejo, C.; Tiong, D. L. Y.; Chan, P. W. H. J. Am. Chem. Soc. 2012, 134, 7344.
[86] Zhang, G.; Ma, Y.; Wang, S.; Zhang, Y.; Wang, R. J. Am. Chem. Soc. 2012, 134, 12334.
[87] Guin, S.; Ghsh, T.; Rout, S. K.; Banerjee, A.; Patel, B. K. Org. Lett. 2011, 13, 5976.
[88] Recent examples for theoretical studies on Cu catalyzed C—H functionalizations, please see:
(a) Santoro, S.; Liao, R.-Z.; Himo, F. J. Org. Chem. 2011, 76, 9246.
(b) Chen, B.; Hou, X.-L.; Li, Y.-X.; Wu, Y.-D. J. Am. Chem. Soc. 2011, 133, 7668.
(c) Wang, M.; Fan, T.; Lin, Z. Organometallics 2012, 31, 560.
(d) Cheng, G.-J.; Song, L.-J.; Yang, Y.-F.; Zhang, X.-H.; Wiest, O.; Wu, Y.-D. ChemSusChem 2013, ASAP (DOI: 10.1002/cplu. 201300117).
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