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Progress in Chemistry 2018, Vol. 30 Issue (9): 1317-1329 DOI: 10.7536/PC180206 Previous Articles   Next Articles

• Review •

Group-Directed C—H Functionalization

Yandong Dou1,2, Xiaoxu Gu2, Jianze Jiang2, Qing Zhu1,2*   

  1. 1. Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Hangzhou 310032, China;
    2. College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou 310014, China
  • Received: Revised: Online: Published:
  • Supported by:
    The work was supported by the National Natural Science Foundation of China (No. 21472172) and the Zhejiang University Student Science and Technology Innovation Program (Xin Miao Talent Program)(No. 2017R403052).
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Transition-metal-catalyzed C—H bond activation is currently one of the most extensively studied research topics in organic synthesis. Recently, the directing group assisted C—H functionlization has drawn more attention from the researchers. The directing groups could enhance the reactive speed, selectivity and catalysis efficiency, which usually contain the nitrogen or oxygen atom. The review aims to summarize the methods of construction of C-C bond, C-O bond or C—N bond by C—H bond activation via introducing a directing group, including carboxyl, pyridnyl groups and so on during the past 3 years. The reaction mechanisms, the existing problems and limitations of this field are also included in this review. Finally, the development trend of this area is prospected.
Contents
1 Introduction
2 Recent advances in directing group C—H activation
2.1 Nitrogen-containing groups as the directing group
2.2 Oxygen-containing groups as the directing group
3 Conclusion
Key words: C—H activation, directing group, transition-metal, azidation, arylation

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[1] a) Qin Y, Zhu L H, Luo S Z. Chem. Rev., 2017, 117:9433; b) Wei Y, Hu P, Zhang M, Su W P. Chem. Rev., 2017, 117:8864
[2] Kawasaki Y, Ishikawa Y, Igawa K, Tomooka K. J. Am. Chem. Soc., 2011, 133:20712
[3] Wang P, Verma P, Xia G, Shi J, Qiao J X, Tao S, Cheng P T W, Poss M A, Farmer M E, Yeung K S, Yu J Q. Nature, 2017, 551:489.
[4] Wu X F, Anbrarasan P, Neumannr H, Beller M. Angew. Chem. Int. Ed., 2010, 49:7316.
[5] Arockiam P B, Bruneau C, Dixneuf P H. Chem. Rev., 2012, 112:5879.
[6] Satoh T, Kawamura Y, Miura M, Nomura M. Angew. Chem. Int. Ed., 1997, 36:1740.
[7] a) Mei T S, Giri R, Maugel N, Yu J Q. Angew. Chem. Int. Ed., 2008, 47:5215; b) Chen X, Hao X S, Goodhue C E, Yu J Q. J. Am. Chem. Soc., 2006, 128:6790.
[8] Tang C H, Jiao N. J. Am. Chem. Soc., 2012, 134:18924.
[9] Fang H, Dou Y D, Ge J Y, Chhabra M, Sun H, Zhang P, Zheng Y G, Zhu Q. J. Org. Chem., 2017, 82:11212.
[10] a) Halima T B, Vandavasi J K, Shkoor M, Newman S G. ACS Catal., 2017, 7:2176; b) Wang J Q, He J, Zhi C, Luo B, Li X M, Pan Y, Cao X Q, Gu H W. RSC Adv., 2014, 4:16607.
[11] a) Xie F, Qi Z S, Li X W. Angew. Chem. Int. Ed., 2013, 52:11862; b) Saidi O, Marafie J, Ledger A E W, Liu P M, Mahon M F, Kohn G K, Whittlesey M K, Frost C G. J. Am. Chem. Soc. 2011, 133:19298; c) Stowers K J, Sanford M S. Org. Lett., 2009, 11:4584.
[12] Lou S J, Chen Q, Wang Y F, Xu D Q, Du X H, He J Q, Mao Y J, Xu Z Y. ACS Catal., 2015, 5:2846.
[13] Wang Z, Kuninobu Y, Kanai M. J. Am. Chem. Soc., 2015, 137:6140.
[14] Pawar G G, Brahmanandan A, Kapur M. Org. Lett., 2016, 18:448.
[15] Ravi M, Allu S, Swamy K C K. J. Org. Chem., 2017, 82:2355.
[16] Xu Y W, Zhou X K, Zheng G F, Li X W. Org. Lett., 2017, 19, 5256.
[17] Zhang G F, Li Y, Xie X Q, Ding C R. Org. Lett., 2017, 19:1216.
[18] McAteer D C, Javed E, Huo L, Huo S. Org. Lett., 2017, 19:1606.
[19] a) Liu B X, Li B, Wang B Q. Chem. Commun., 2015, 51:16334; b) Wang X, Qiu R H, Yan C Y, Reddy V P, Zhu L Z, Xu X H, Yin S F. Org. Lett., 2015, 17:1970; c) Yan S B, Zhang S, Duan W L. Org. Lett., 2015, 17:2458; d) Yan Q Q, Chen Z K, Yu W L, Yin H, Liu Z X, Zhang Y H. Org. Lett., 2015, 17:2482.
[20] Seuss A M, Ertem M Z, Cramer C J, Stahl S S. J. Am. Chem. Soc., 2013, 135:9797.
[21] Qiao H, Sun S Y, Yang F, Zhu Y, Zhu W G, Dong Y, Wu Y S, Kong X T, Jiang L, Wu Y J. Org. Lett., 2015, 17:6086.
[22] Wei J, Jiang J X, Xiao X S, Lin D E, Deng Y F, Ke Z F, Jiang W, Zeng W. J. Org. Chem., 2016, 81:946.
[23] Liu X G, Xu J, Shen C, Zhu X L, Zhang P F, Ajitha M J, Huang K W, An Z F. Chem. Asian J., 2016, 11:882.
[24] Wang Z, Kuninobu Y, Kanai M. Org. Lett., 2014, 16:4790.
[25] Tan Z, Zhu G G. Chem. Commoun., 2016, 52:6845.
[26] Takamatsu D, Hirano K, Miura M. Org. Lett., 2015, 17:4066.
[27] Dou Y D, Xie Z D, Sun Z G, Fang H L, Shen C, Zhang P F, Zhu Q. ChemCatChem., 2016, 8:3570.
[28] Lang K, Davis L, Wallace S, Mahesh M, Cox D J, Blackman M L, Fox J M, Chin J W. J. Am. Chem. Soc., 2012, 134:10317.
[29] Lemieux G A, Graffenried C L, Bertozzi C R. J. Am. Chem. Soc., 2003, 125:4708.
[30] Testa C, Gigot E, Genc S, Decrau R, Roger J, Hierso J. Angew. Chem., 2016, 128:5645.
[31] Mboyi C D, Testa C, Reeb S, Genc S, Cattey H, Lessard P F, Roger J, Hierso J C. ACS Catal., 2017, 7:8493.
[32] Peng Z H, Yu Z, Li T, Li N, Wang Y L, Song L H, Jiang C Y. Organometallics., 2017, 36:2826.
[33] a) Krajcovicova S, Soural M. ACS Comb. Sci., 2016, 18:371; b) Zhou L H, Zhang H W, Tao S J, Ehteshami M, Cho J H, McBrayer T R, Tharnish P, Whitaker T, Amblard F, Coats S J, Schinaz R F, ACS Med. Chem. Lett., 2016, 7:17; c) Keough D T, Adams T S, Jones M K, Brereton M, Guddat L W, Jersey J, J. Med. Chem., 2006, 49:7479.
[34] Guo H M, Jiang L L, Niu H Y, Rao W H, Liang L, Mao R Z, Li D Y, Qu G R. Org. Lett., 2011, 13:2008.
[35] Kim H J, Ajitha M J, Lee Y, Ryu J, Kim J, Lee Y, Jung Y, Chang S. J. Am. Chem. Soc., 2014, 136:1132.
[36] Yu M Y, Wang Z Q, Tian M, Lu C H, Li S L, Du H G. J. Org. Chem., 2016, 81:3435.
[37] Ruan Z, Lackner S, Ackermann L. ACS Catal., 2016, 6:4690.
[38] Warratz S, Burns D J, Zhu C, Korvorapun K, Rogge T, Scholz J, Jooss C, Gelman D, Ackermann L. Angew. Chem. Int. Ed., 2017, 56:1557.
[39] Bettadapur K R, Lanke V, Ramaiah P K. Org. Lett. 2015, 17:4658.
[40] Potter T J, Kamber D N, Mercado B Q, Ellman J A. ACS Catal., 2017, 7:150.
[41] Xu J C, Liu Y, Wang Y, Li Y J, Xu X H, Jin Z. Org. Lett., 2017, 19:1562.
[42] Hoque M E, Bisht R, Haldar C, Chattopadhyay B. J. Am. Chem. Soc., 2017, 139:7745.
[43] Sato T, Yoshida T, Mamari H H A, Ilies L, Nakamura E. Org. Lett., 2017, 19:5458.
[44] Cheng H C, Hernandez J G, Bolm C. Org. Lett., 2017, 19:6284.
[45] a) Miao J M, Yang K, Kurek M, Ge H B. Org. Lett., 2015, 17:3738; b)He J, Takise R, Fu H Y, Yu J Q. J. Am. Chem. Soc., 2015, 137:4618.
[46] Zhu R Y, Denis T G S, Shao Y, He J, Sieber J D, Senanayake C H, Yu J Q. J. Am. Chem. Soc., 2017, 139:5724.
[47] Zhu C L, Zhang Y F, Kan J, Zhao H Q, Su W P. Org. Lett., 2015, 17:3418.
[48] Biafora A, Krause T, Hackenberger D, Belitz F, Goossen L J, Angew. Chem. Int. Ed., 2016, 55:14752.
[49] Mei R, Zhang S K, Ackermann L. Org. Lett., 2017, 19:3171.
[50] Mandal A, Dana S, Sahoo H, Sankar G, Baidya G M. Org. Lett., 2017, 19:2430.
[51] Aman A, Wulff W D. Synthesis, 2010, 21:3670.
[52] Zhao Y T, Huang B B, Yang C, Li B, Gou B Q, Xia W J. ACS Catal., 2017, 7:2446.
[53] Tan E, Konovalov A I, Fernandez G A, Dorel R, Echavarren A M. Org. Lett., 2017, 19:5561
[54] a) Putro W S, Kojima T, Hara T, Ichikuni N, Shimazu S. Catal. Sci. Technol., 2017, 7:3637; b) Yu H, Ru S, Dai G Y, Zhai Y Y, Lin H L, Han S, Wei Y G. Angew. Chem. Int. Ed., 2017, 56:3867.
[55] Bisht R, Chattopadhyay B. J. Am. Chem. Soc., 2016, 138:84.
[56] Zhang F L, Hong K, Li T J, Park H, Yu J Q. Science, 2016, 351:252.
[57] Liu X H, Park H, Hu J H, Hu Y, Zhang Q L, Wang B L, Sun B, Yeung K S, Zhang F L, Yu J Q. J. Am. Chem. Soc., 2017, 139:888.
[58] Ma F, Lei M, Hu L H. Org. Lett., 2016, 18:2708.
[59] Yang F Z, Rauch K, Kettelhoit K, Ackermann L. Angew. Chem. Int. Ed., 2014, 53:11285.
[60] Chen X Y, Ozturk S, Sorensen E J. Org. Lett., 2017, 19:6280.
[61] Yang K, Li Q, Liu Y B, Li G G, Ge H B. J. Am. Chem. Soc., 2016, 138:12775.
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Abstract

Group-Directed C—H Functionalization