European Journal of Chemistry

Recent advance in direct sp3 carbon-hydrogen bond functionalizations



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Xiao-Hua Cai
Jun Jin
Bing Xie

Abstract

Direct and selective carbon-hydrogen bond functionalization has attracted enormous attention because it provides more efficient strategies for preparing valuable functional molecules from easily available substrates. Significant and exciting developments in functionalization of un-activation Csp3-H bonds have continuously been made over the past few decades. This review mainly summarizes recent advances on direct Csp3-H bond functionalization for the formation of C-C and C-heteroatom bond under transition-metal-catalysed and metal-free conditions.


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Cai, X.-H.; Jin, J.; Xie, B. Recent Advance in Direct Sp3 Carbon-Hydrogen Bond Functionalizations. Eur. J. Chem. 2016, 7, 248-270.

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References

[1]. Borovik, A. S. Chem. Soc. Rev. 2011, 40, 1870-1874.
http://dx.doi.org/10.1039/c0cs00165a

[2]. Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976-1991.
http://dx.doi.org/10.1039/c0cs00182a

[3]. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068-5083.
http://dx.doi.org/10.1039/c1cs15082k

[4]. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem. Int. Ed. 2012, 51, 8960-9009.
http://dx.doi.org/10.1002/anie.201201666

[5]. Wencel-Delord, J.; Glorius, F. Angew. Chem. Int. Ed. 2012, 51, 10236-10254.
http://dx.doi.org/10.1002/anie.201203269

[6]. Kuhl, N.; Hoplinson, M. N.; Chen, D. Y. K.; Youn, S. W. Chem. Eur. J. 2012, 18, 9452-9474.
http://dx.doi.org/10.1002/chem.201201329

[7]. Gao, K.; Yoshikai, N. Acc. Chem. Res. 2014, 47, 1208-1219.
http://dx.doi.org/10.1021/ar400270x

[8]. Wencel-Delord, J.; Glorius, F. Nat. Chem. 2013, 5, 369-375.
http://dx.doi.org/10.1038/nchem.1607

[9]. Li, B.; Dixneuf, P. H. Chem. Soc. Rev. 2013, 42, 5744-5767.
http://dx.doi.org/10.1039/c3cs60020c

[10]. Sarkar, S. D.; Liu, W.; Kozhushkov, S. I.; Ackermann, L. Adv. Synth. Catal. 2014, 356, 1461-1479.
http://dx.doi.org/10.1002/adsc.201400110

[11]. Cai, X. H. Xie, B. Curr. Org. Chem. 2015, 19, 121-150.
http://dx.doi.org/10.2174/1385272819666141027230851

[12]. Cai, X. H. Xie, B. Synthesis 2015, 47, 737-759.
http://dx.doi.org/10.1055/s-0034-1379720

[13]. Cai, X. H. Xie, B. Arkivoc 2015, 1, 184-210.

[14]. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780-1824.
http://dx.doi.org/10.1021/cr100379j

[15]. Engle, K. M.; Mei, T. S.; Wasa, M.; Yu, J. Q. Acc. Chem. Res. 2011, 45, 788-802.
http://dx.doi.org/10.1021/ar200185g

[16]. Davies, H. M. L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857-1869.
http://dx.doi.org/10.1039/c0cs00217h

[17]. Zhang, S. Y.; Zhang, F. M.; Tu, Y. Q. Chem. Soc. Rev. 2011, 40, 1937-1949.
http://dx.doi.org/10.1039/c0cs00063a

[18]. Newhouse, T.; Baran, P. S. Angew. Chem., Int. Ed. 2011, 50, 3362-3374.
http://dx.doi.org/10.1002/anie.201006368

[19]. White, M. C. Science, 2012, 335, 807-809.
http://dx.doi.org/10.1126/science.1207661

[20]. Roizen, J. L.; Harvey, M. E.; Du, B. J. Acc. Chem. Res. 2012, 45, 911-922.
http://dx.doi.org/10.1021/ar200318q

[21]. Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3464-3484.
http://dx.doi.org/10.1039/c2cs15323h

[22]. Rouquet, G.; Chatani, N. Angew. Chem. Int. Ed. 2013, 52, 11726-11743.
http://dx.doi.org/10.1002/anie.201301451

[23]. Girard, S. A.; Knauber, T.; Li, C. J. Angew. Chem. Int. Ed. 2014, 53, 74-100.
http://dx.doi.org/10.1002/anie.201304268

[24]. Zhang, W.; Wang, N. X.; Xing, Y. Synlett. 2015, 26, 2088-2098.
http://dx.doi.org/10.1055/s-0034-1381031

[25]. Vachhani, D. D.; Galli, M.; Jacobs, J.; Meervelt, L. V.; Der Eycken, E, V. V. Chem. Commun. 2013, 49, 7171-7173.
http://dx.doi.org/10.1039/c3cc43418d

[26]. Zhang, G.; Ma, Y. X.; Cheng, G. B.; Liu, D. B.; Wang, R. Org. Lett. 2014, 16, 656-659.
http://dx.doi.org/10.1021/ol500045p

[27]. Ma, Y. H.; Zhang, S. A.; Yang, S. P.; Song, F. J.; You, J. S. Angew. Chem. 2014, 126, 8004-8008.
http://dx.doi.org/10.1002/ange.201402475

[28]. Xie, J.; Shi, S.; Zhang, T.; Mehrkens, N.; Rudolph, M. A.; Hashmi S. K. Angew. Chem. Int. Ed. 2015, 54, 6046-6050.
http://dx.doi.org/10.1002/anie.201412399

[29]. Sundararaju, B.; Achard, M.; Sharma, G. V. M.; Bruneau, C. J. Am. Chem. Soc. 2011, 133, 10340-10344.
http://dx.doi.org/10.1021/ja203875d

[30]. Piou, T.; Neuville, L.; Zhu, J. P. Angew. Chem. 2012, 124, 11729-11733.
http://dx.doi.org/10.1002/ange.201206267

[31]. Zhang, L.; Peng, C.; Zhao, D.; Wang, Y.; Fu, H. J.; Shen, Q.; Li, J. X. Chem. Commun. 2012, 48, 5928-5930.
http://dx.doi.org/10.1039/c2cc32009f

[32]. Li, Z. J.; Zhang, Y.; Zhang, L. Z.; Liu, Z. Q. Org. Lett. 2014, 16, 382-385.
http://dx.doi.org/10.1021/ol4032478

[33]. Gharpure, S. J.; Shelke, Y. G.; Reddy, S. R. B. RSC Adv. 2014, 4, 46962-46965.
http://dx.doi.org/10.1039/C4RA08421G

[34]. Yan, J. X.; Li, H.; Liu, X. W.; Shi, J. L.; Wang, X.; Shi, Z. J. Angew. Chem. 2014, 126, 5045-5049.
http://dx.doi.org/10.1002/ange.201402562

[35]. Zhang, Q.; Yin, X. S.; Zhao, S.; Fang, S. L.; Shi, B. F. Chem. Commun. 2014, 50, 8353-8355.
http://dx.doi.org/10.1039/c4cc03615h

[36]. Kulago, A. A.; Van Steijvoort, B. F.; Mitchell, E. A.; Meerpoel, L.; Maes, B. U. W. Adv. Synth. Catal. 2014, 356, 1610-1618.
http://dx.doi.org/10.1002/adsc.201400117

[37]. Yan, H.; Lu, L. H.; Rong, G. W.; Liu, D. F.; Zheng, Y.; Chen, J.; Mao, J. C. J. Org. Chem. 2014, 79, 7103-7111.
http://dx.doi.org/10.1021/jo501274f

[38]. Yang, X. H.; Wei, W. T.; Li, H. B.; Song, R. J.; Li, J. H. Chem. Commun. 2014, 50, 12867-12869.
http://dx.doi.org/10.1039/C4CC05051G

[39]. Peng, J.; Chen, C.; Chen, J. J.; Su, X.; Xi, C. J.; Chen, H. C. Org. Lett. 2014, 16, 3776-3779.
http://dx.doi.org/10.1021/ol501655g

[40]. Cheng, J. K.; Loh, T. P. J. Am. Chem. Soc. 2015, 137, 42-45.
http://dx.doi.org/10.1021/ja510635k

[41]. Pan, C. D.; Zhang, H. L.; Zhu, C. J. Org. Biomol. Chem. 2015, 13, 361-364.
http://dx.doi.org/10.1039/C4OB02172J

[42]. Wang, Y. X.; Peng, F. F.; Liu, J.; Huo, C. D.; Wang, X. C.; Jia, X. D. J. Org. Chem. 2015, 80, 609-614.
http://dx.doi.org/10.1021/jo502184k

[43]. Muramatsu, W.; Nakano, K. Org. Lett. 2015, 17, 1549-1552.
http://dx.doi.org/10.1021/acs.orglett.5b00434

[44]. He, J.; Takise, R.; Fu, H. Y.; Yu, J. Q. J. Am. Chem. Soc. 2015, 137, 4618-4621.
http://dx.doi.org/10.1021/jacs.5b00890

[45]. Guo, S. R.; Yuan, Y. Q.; Xiang, J. N. New J. Chem. 2015, 39, 3093-3097.
http://dx.doi.org/10.1039/C4NJ02416H

[46]. Zhang, G. F.; Xie, X. Q.; Zhu, J. F.; Li, S. S.; Ding, C. R.; Ding, P. Org. Biomol. Chem. 2015, 13, 5444-5449.
http://dx.doi.org/10.1039/C5OB00066A

[47]. Liu, Y. J.; Zhang, Z. Z.; Yan, S. Y.; Liu, Y. H.; Shi. B. F. Chem. Commun. 2015, 51, 7899-7902.
http://dx.doi.org/10.1039/C5CC02254A

[48]. Li, L.; Xia, X. H.; Wang, Y.; Bora, P. P.; Kang, Q. Adv. Synth. Catal. 2015, 357, 2089-2097.
http://dx.doi.org/10.1002/adsc.201500396

[49]. Mitsudera, H.; Li, C. J. Tetrahedron Lett. 2011, 52, 1898-1900.
http://dx.doi.org/10.1016/j.tetlet.2011.02.038

[50]. Liu, J. M.; Yi, H.; Zhang, X.; Liu, C.; Liu, R.; Zhang, G. T.; Lei, A. W. Chem. Commun. 2014, 50, 7636-7638.
http://dx.doi.org/10.1039/c4cc02275k

[51]. Li, W. P.; Zhu, X. B.; Mao, H. B.; Tang, Z. H.; Cheng, Y. X.; Zhu, C. J. Chem. Commun. 2014, 50, 7521-7523.
http://dx.doi.org/10.1039/c4cc02768j

[52]. Pedroni, J.; Boghi, M.; Saget, T.; Cramer, N. Angew. Chem. Int. Ed. 2014, 53, 9064-9067.
http://dx.doi.org/10.1002/anie.201405508

[53]. Curto, J. M.; Kozlowski, M. C. J. Am. Chem. Soc. 2015, 137, 18-21.
http://dx.doi.org/10.1021/ja5093166

[54]. Zhou, L. L.; Tang, S.; Qi, X. T.; Lin, C. T.; Liu, K.; Liu, C.; Lan, Y.; Lei, A. W. Org. Lett. 2014, 16, 3404-3407.
http://dx.doi.org/10.1021/ol501485f

[55]. Wang, N. C.; Li, R. H.; Li, L. B.; Xu, S. S.; Song, H. B.; Wang, B. Q. J. Org. Chem. 2014, 79, 5379-5385.
http://dx.doi.org/10.1021/jo5008515

[56]. Zhu, Z. Q.; Wang, T. T.; Bai, P.; Huang, Z. Z. Org. Biomol. Chem. 2014, 12, 5839-5842.
http://dx.doi.org/10.1039/C4OB01256A

[57]. Wu, X. S.; Zhao, Y.; Ge, H. B. Chem. Eur. J. 2014, 20, 9530-9533.
http://dx.doi.org/10.1002/chem.201403356

[58]. Chen, X. L.; Chen, T. Q.; Ji, F. Y.; Zhou, Y. B.; Yin. S. F. Catal. Sci. Technol. 2015, 5, 2197-2202.
http://dx.doi.org/10.1039/C4CY01618A

[59]. He, J.; Shigenari, T.; Yu, J. Q. Angew. Chem. Int. Ed. 2015, 54, 6545-6549.
http://dx.doi.org/10.1002/anie.201502075

[60]. Zhao, J. C.; Fang, H.; Zhou, W.; Han, J. L.; Pan, Y. J. Org. Chem. 2014, 79, 3847-3855.
http://dx.doi.org/10.1021/jo500192h

[61]. Luo, X. Y.; Wang, Z. L.; Jin, J. H.; An, X. L.; Shen, Z. L.; Deng, W. P. C. Tetrahedron 2014, 70, 8226-8230.
http://dx.doi.org/10.1016/j.tet.2014.09.031

[62]. Chen, C.; Xu, X. H.; Yang, B.; Qing, F. L. Org. Lett. 2014, 16, 3372-3375.
http://dx.doi.org/10.1021/ol501400u

[63]. Lin, C.; Yu, W. L.; Yao, J. Z.; Wang, B. J.; Liu, Z. X.; Zhang, Y. H. Org. Lett. 2015, 17, 1340-1343.
http://dx.doi.org/10.1021/acs.orglett.5b00471

[64]. Chen, D. F.; Han, Z. Y.; He, Y. P.; Yu, J.; Gong, L. Z. Angew. Chem. 2012, 51, 12307-23310.
http://dx.doi.org/10.1002/anie.201205062

[65]. Zhang, G.; Wang, S. L.; Ma, Y. X.; Kong, W. D.; Wang, R. Adv. Synth. Catal. 2013, 355, 874-879.
http://dx.doi.org/10.1002/adsc.201200731

[66]. Cao, J. J.; Zhu, T. H.; Wang, S. Y.; Gu, Z. Y.; Wang, X.; Ji, S. J. Chem. Commun. 2014, 50, 6439-6442.
http://dx.doi.org/10.1039/c4cc00743c

[67]. Xie, Z. Y.; Liu, L.; Chen, W. F.; Zheng, H. B. Xu, Q. Q.; Yuan, H. Q.; Lou, H. X. Angew. Chem. 2014, 126, 3985-3989.
http://dx.doi.org/10.1002/ange.201310193

[68]. Shao, Z. Z.; Wang, L.; Xu, L. B.; Zhao, H. L.; Xiao, J. RSC Adv. 2014, 4, 53188-53191.
http://dx.doi.org/10.1039/C4RA09338K

[69]. Wang, X. H.; Wang, Y.; Yuan, Y.; Xing, C. H. Tetrahedron 2014, 70, 2195-2202.
http://dx.doi.org/10.1016/j.tet.2014.01.033

[70]. Hu, W.; Lin, J. P.; Song, L. R.; Long, Y. Q. Org. Lett. 2015, 17, 1268-1271.
http://dx.doi.org/10.1021/acs.orglett.5b00248

[71]. Zhao, J. C.; Fang, H.; Song, R. C.; Zhou, J.; Han, J. L.; Pan, Y. Chem. Commun. 2015, 51, 599-602.
http://dx.doi.org/10.1039/C4CC07654K

[72]. Gao, Q. H.; Fei, Z.; Zhu, Y. P.; Lian, M.; Jia, F. C.; Liu, M. C.; She, N. F.; Wu, A. X. Tetrahedron 2013, 69, 22-28.
http://dx.doi.org/10.1016/j.tet.2012.10.072

[73]. Kalmode, H. P.; Vadagaonkar, K. S.; Chaskar, A. C. RSC Adv. 2014, 4, 60316-60326.
http://dx.doi.org/10.1039/C4RA07556K

[74]. Rajeshkumar, V.; Chandrasekar, S.; Sekar, G. Org. Biomol. Chem. 2014, 12, 8512-8518.
http://dx.doi.org/10.1039/C4OB01564A

[75]. Zhang, X. S.; Wang, M.; Li, P. H.; Wang, L. Chem. Commun. 2014, 50, 8006-8009.
http://dx.doi.org/10.1039/c4cc01189a

[76]. Dian, L. Y.; Wang, S. S.; Zhang-Negrerie, D.; Du, Y. F.; Zhao, K. Chem. Commun. 2014, 50, 11738-11741.
http://dx.doi.org/10.1039/C4CC05758A

[77]. Zhang, N. N.; Cheng, R.; Zhang-Negrerie, D.; Du, Y. F.; Zhao, K. J. Org. Chem. 2014, 79, 10581-10587.
http://dx.doi.org/10.1021/jo5016823

Supporting Agencies

The National Natural Science Foundation of China (21562016), the Natural Science Foundation of the Guizhou Science and Technology Depart-ment (JZ [2014]2010) and the Science and Technology Planing Project of Guiyang city [(2012204)23], China.
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