European Journal of Chemistry

Recent advance in direct sp3 carbon-hydrogen bond functionalizations



Main Article Content

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.


icon graph This Abstract was viewed 2509 times | icon graph Article PDF downloaded 833 times

How to Cite
(1)
Cai, X.-H.; Jin, J.; Xie, B. Recent Advance in Direct Sp3 Carbon-Hydrogen Bond Functionalizations. Eur. J. Chem. 2016, 7, 248-270.

Article Details

Share
Crossref - Scopus - Google - European PMC
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

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).