Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3084-3104.DOI: 10.6023/cjoc201905027 Previous Articles Next Articles
Special Issue: 碳氢活化合辑2018-2019
收稿日期:
2019-05-13
发布日期:
2019-07-09
通讯作者:
罗飞华
E-mail:20180011@yznu.edu.cn
基金资助:
Received:
2019-05-13
Published:
2019-07-09
Contact:
Luo Feihua
E-mail:20180011@yznu.edu.cn
Supported by:
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Luo Feihua. Progress in Transition Metal Catalyzed C-H Functionalization Directed by Carboxyl Group[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3084-3104.
[1] |
(a) Zhang, B.; Guan, H.; Liu, B.; Shi, B. Chin. J. Org. Chem. 2014, 34, 1487 (in Chinese).
doi: 10.6023/cjoc201405011 |
(张博, 管晗曦, 刘斌, 史炳锋, 有机化学, 2014, 34, 1487.)
doi: 10.6023/cjoc201405011 |
|
(b) Yuan, Y.; Song, S.; Jiao, N. Acta Chim. Sinica 2015, 73, 1231 (in Chinese).
doi: 10.6023/cjoc201405011 |
|
(袁逸之, 宋颂, 焦宁, 化学学报, 2015, 73, 1231.)
doi: 10.6023/cjoc201405011 |
|
(c) Zhao, J.; Zhang, Q. Acta Chim. Sinica 2015, 73, 1235 (in Chinese).
doi: 10.6023/cjoc201405011 |
|
(赵金钵, 张前, 化学学报, 2015, 73, 1235.)
doi: 10.6023/cjoc201405011 |
|
(d) Ding, H.; Li, J.; Guo, Q.; Xiao, Y. Chin. J. Org. Chem. 2017, 37, 3112 (in Chinese).
doi: 10.6023/cjoc201405011 |
|
(丁怀伟, 李娟, 郭庆辉, 肖琰, 有机化学, 2017, 37, 3112.)
doi: 10.6023/cjoc201405011 |
|
(e) Cheng, H.; Lin, J.; Zhang, Y.; Chen, B.; Wang, M.; Cheng, L.; Ma, J. Chin. J. Org. Chem. 2019, 39, 318 (in Chinese).
doi: 10.6023/cjoc201405011 |
|
(程辉成, 林锦龙, 张耀丰, 陈冰, 王敏, 程丽华, 马姣丽, 有机化学学, 2019, 39, 318.)
doi: 10.6023/cjoc201405011 |
|
[2] |
(a) Zhang, F.; Spring, D. Chem. Soc. Rev. 2014, 43, 6906.
doi: DOI: 10.6023/A1512E001 |
(b) Chen, Z.; Wang, B.; Zhang, J.; Yu, W.; Liu, Z.; Zhang, Y. Org. Chem. Front. 2015, 2, 1107.
doi: DOI: 10.6023/A1512E001 |
|
(c) Yu, J.; Ding, K. Acta Chim. Sinica 2015, 73, 1223 (in Chinese).
doi: DOI: 10.6023/A1512E001 |
|
(余金权, 丁奎岭, 化学学报, 2015, 73, 1223.)
doi: DOI: 10.6023/A1512E001 |
|
[3] |
(a) Drapeau, M.; Gooßen, L. Chem.-Eur. J. 2016, 22, 18654.
doi: 10.1002/chem.v22.52 |
(b) Font, M.; Quibell, J.; Perry, G.; Larrosa, L. Chem. Commun. 2017, 53, 5584.
doi: 10.1002/chem.v22.52 |
|
[4] |
Miura M. Tsuda T. Satoh T. Pivsa-Art S. Nomura M. J. Org. Chem. 1998 63 5211.
doi: 10.1021/jo980584b |
[5] |
Suresh R. R. Swamy K. C. K. J. Org. Chem. 2012 77 6959.
doi: 10.1021/jo301149s |
[6] |
Nandi D. Ghosh D. Chen S. Kuo B. Wang N. Lee H. J. Org. Chem. 2013 78 3445.
doi: 10.1021/jo400174w |
[7] |
Ackermann L. Pospech J. Graczyk K. Rauch K. Org. Lett. 2012 14 930.
doi: 10.1021/ol2034614 |
[8] |
Chinnagolla R. K. Jeganmohan M. Chem. Commun. 2012 48 2030.
doi: 10.1039/c2cc16916a |
[9] |
Warratz S. Kornhaaß C. Cajaraville A. Niepötter B. Stalke D. Ackermann L. Angew. Chem., Int. Ed. 2015 54 5513.
doi: 10.1002/anie.201500600 |
[10] |
Huang L. Biafora A. Zhang G. Bragoni V. Gooßen L. Angew. Chem., Int. Ed. 2016 55 6933.
doi: 10.1002/anie.201600894 |
[11] |
Liu Y. Yang Y. Shi Y. Wang X. Zhang L. Cheng Y. You J. Organometallics 2016 35 1350.
doi: 10.1021/acs.organomet.6b00107 |
[12] |
Yu C. Zhang J. Zhong G. Chem. Commun. 2017 53 9902.
doi: 10.1039/C7CC04973K |
[13] |
Han W.; F. Pu F. Fan J. Liu Z. Shi X. Adv. Synth. Catal. 2017 359 3520.
doi: 10.1002/adsc.201700603 |
[14] |
Trita A. Biafora A. Drapeau M. Weber P. Gooßen L. Angew. Chem., Int. Ed. 2018 57 14580.
doi: 10.1002/anie.201712520 |
[15] |
Jambu S. Tamizmani M. Jeganmohan M. Org. Lett. 2018 20 1982.
doi: 10.1021/acs.orglett.8b00533 |
[16] |
(a) Hu, X.; Hu, Z.; Zhang, G.; Sivendran, N.; Gooßen, L. Org. Lett. 2018, 20, 4337.
doi: 10.1021/acs.orglett.8b01762 |
(b) Hu, X.; Hu, Z.; Trita, A.; Zhang, G.; Gooßen, L. Chem. Sci. 2018, 9, 5289.
doi: 10.1021/acs.orglett.8b01762 |
|
[17] |
Dana S. Mandal A. Sahoo H. Mallik S. Grandhi G. Baidya M. Org. Lett. 2018 20 716.
doi: 10.1021/acs.orglett.7b03852 |
[18] |
Giri R. Maugel N. Li J. Wang D. Breazzano S. Saunders L. Yu J. J. Am. Chem. Soc. 2007 129 3510.
doi: 10.1021/ja0701614 |
[19] |
Chiong H. Pham Q. Daugulis O. J. Am. Chem. Soc. 2007 129 9879.
doi: 10.1021/ja071845e |
[20] |
Wu Z. Chen S. Hu C. Li Z. Xiang H. Zhou X. ChemCatChem 2013 5 2839.
doi: 10.1002/cctc.201300470 |
[21] |
Zhu C. Zhang Y. Kan J. Zhao H. Su W. Org. Lett. 2015 17 3418.
doi: 10.1021/acs.orglett.5b01398 |
[22] |
Huang L. Hackenberger H. Gooßen L. Angew. Chem., Int. Ed. 2015 54 12607.
doi: 10.1002/anie.201505769 |
[23] |
Simonetti M. Cannas D. Panigrahi A. Kujawa S. Kryjewski M. Xie P. Larrosa L. Chem.-Eur. J. 2017 23 549.
doi: 10.1002/chem.201605068 |
[24] |
Gong H. Zeng H. Zhou F. Li C. Angew. Chem., Int. Ed. 2015 54 5718.
doi: 10.1002/anie.201500220 |
[25] |
Qin X. Li X. Huang Q. Liu H. Wu D. Guo Q. Lan J. Wang R. You J. Angew. Chem., Int. Ed. 2015 54 7167.
doi: 10.1002/anie.201501982 |
[26] |
Sun D. Li B. Lan J. Huang Q. You J. Chem. Commun. 2016 52 3635.
doi: 10.1039/C6CC00103C |
[27] |
Tan G. You Q. Lan J. You J. Angew. Chem., Int. Ed. 2018 57 6309.
doi: 10.1002/anie.201802539 |
[28] |
Mei R. Zhang S. Ackermann L. Org. Lett. 2017 19 3171.
doi: 10.1021/acs.orglett.7b01294 |
[29] |
Zhang Y. H. Shi B. F. Yu J. Q. Angew. Chem., Int. Ed. 2009 48 6097.
doi: 10.1002/anie.200902262 |
[30] |
Ackermann L. Pospech J. Org. Lett. 2011 13 4153.
doi: 10.1021/ol201563r |
[31] |
Shi X. Li C. Adv. Synth. Catal. 2012 354 2933.
doi: 10.1002/adsc.201200690 |
[32] |
Boun P. Villa G. Dang D. Richardson P. Su S. Yu J. J. Am. Chem. Soc. 2013 135 17508.
doi: 10.1021/ja409014v |
[33] |
Cheng G. Li T. Yu J. J. Am. Chem. Soc. 2015 137 10950.
doi: 10.1021/jacs.5b07507 |
[34] |
Han W. Pu F. Li C. Liu Z. Fan J. Shi X. Adv. Synth. Catal. 2018 360 1358.
doi: 10.1002/adsc.201701468 |
[35] |
Kumar G. Chand T. Singh D. Kapur M. Org. Lett. 2018 20 4934.
doi: 10.1021/acs.orglett.8b02064 |
[36] |
Giri R. Yu J. J. Am. Chem. Soc. 2008 130 14082.
doi: 10.1021/ja8063827 |
[37] |
Shi X. Renzetti A. Kundu S. Li C. Adv. Synth. Catal. 2013 356 723.
doi: 10.1002/adsc.v356.4 |
[38] |
Manone P. Danoun G. Gooßen L. Angew. Chem. Int. Ed. 2013 52 6704.
doi: 10.1002/anie.201301328 |
[39] |
Mao J. Ge H. Org. Lett. 2013 15 2930.
doi: 10.1021/ol400919u |
[40] |
Arzoumanidis G. Rauch F. J. Org. Chem. 1981 46 3930.
doi: 10.1021/jo00332a042 |
[41] |
Ng K. Ng F. Yu W. Chem. Commun. 2012 48 11680.
doi: 10.1039/c2cc36502b |
[42] |
Ng F. Zhou Z. Yu W. Chem.-Eur. J. 2014 20 4474.
doi: 10.1002/chem.201304855 |
[43] |
Lee D. Chang S. Chem.-Eur. J. 2015 21 5364.
doi: 10.1002/chem.201500331 |
[44] | Sen A. Kao L. C. J. Chem. Soc., Chem. Commun. 1991 1242. |
[45] |
Dangel B. D. Johnson J. A. Sames D. J. Am. Chem. Soc. 2001 123 8149.
doi: 10.1021/ja016280f |
[46] |
Lee J. M. Chang S. Tetrahedron Lett. 2006 47 1375.
doi: 10.1016/j.tetlet.2005.12.104 |
[47] |
Novák P. Correa A. Gallardo-Donaire J. Martin R. Angew. Chem., Int. Ed. 2011 50 12236.
doi: 10.1002/anie.201105894 |
[48] |
Fraunhoffer K. J. Prabagaran N. Sirois L. E. White M. C. J. Am. Chem. Soc. 2006 128 9032.
doi: 10.1021/ja063096r |
[49] |
Takenaka K. Akita M. Tanigaki Y. Takizawa S. Sasai H. Org. Lett. 2011 13 3506.
doi: 10.1021/ol201314m |
[50] | Taktak S. Flook M. Foxman B. Que L. Rybak-Akimova E. Chem. Commun. 2005 42 5301. |
[51] |
Zhang Y. Yu J. J. Am. Chem. Soc. 2009 131 14654.
doi: 10.1021/ja907198n |
[52] |
Cheng X. F. Li Y. Su Y. M. Yin F. Wang J. Y. Sheng J. Vora H. U. Wang X. S. Yu J. Q. J. Am. Chem. Soc. 2013 135 1236.
doi: 10.1021/ja311259x |
[53] |
Yang M. Y. Jiang X. Y. Shi W. J. Zhu Q. L. Shi Z. J. Org. Lett. 2013 15 690.
doi: 10.1021/ol303569b |
[54] |
Li Y. Ding Y. J. Wang J. Y. Su Y. M. Wang X. S. Org. Lett. 2013 15 2574.
doi: 10.1021/ol400877q |
[55] |
Gallardo-Donaire J. Martin R. J. Am. Chem. Soc. 2013 135 9350.
doi: 10.1021/ja4047894 |
[56] |
Mandal A. Dana S. Sahoo H. Grandhi G. Baidya M. Org. Lett. 2017 19 2430.
doi: 10.1021/acs.orglett.7b00996 |
[57] |
Mei T. Giri R. Maugel N. Yu J. Angew. Chem., Int. Ed. 2008 47 5215.
doi: 10.1002/anie.200705613 |
[58] |
Mei T. Wang D. Yu J. Org. Lett. 2010 12 3140.
doi: 10.1021/ol1010483 |
[59] |
Erbing E. Sanz-Marco A. Vázquez-Romero A. Malmberg J. Johansson M. Gómez-Bengoa E. Martín-Matute B. ACS Catal. 2018 8 920.
doi: 10.1021/acscatal.7b02987 |
[60] |
Ma S. Villa G. Thuy-Boun P. Homs A. Yu J. Angew. Chem., Int. Ed. 2014 53 734.
doi: 10.1002/anie.201305388 |
[61] |
Cornella J. Righi M. Larrosa I. Angew. Chem., Int. Ed. 2011 50 9429.
doi: 10.1002/anie.201103720 |
[62] |
Luo J. Preciado S. Larrosa I. J. Am. Chem. Soc. 2014 136 4109.
doi: 10.1021/ja500457s |
[63] |
Font M. Spencer A. Larrosa I. Chem. Sci. 2018 9 7133.
doi: 10.1039/C8SC02417K |
[64] |
Johnston A. Ling K. Sale D. Lebrasseur N. Larrosa I. Org. Lett. 2016 18 6094.
doi: 10.1021/acs.orglett.6b03085 |
[65] |
Zhang U. Zhao H. Zhang M. Su W. Angew. Chem., Int. Ed. 2015 54 3817.
doi: 10.1002/anie.201411701 |
[66] |
Qin X. Sun D. You Q. Cheng Y. Lan J. You J. Org. Lett. 2015 17 1762.
doi: 10.1021/acs.orglett.5b00532 |
[67] |
Pu F. Zhang L. Liu Z. Shi X. Adv. Synth. Catal. 2018 360 2644.
doi: 10.1002/adsc.201800333 |
[68] |
Wang Z. Yang M. Yang Y. Org. Lett. 2018 20 3001.
doi: 10.1021/acs.orglett.8b01033 |
[69] |
Maehara A. Tsurugi H. Satoh T. Miura M. Org. Lett. 2008 10 1159.
doi: 10.1021/ol8000602 |
[70] |
Mochida S. Hirano K. Satoh T. Miura M. J. Org. Chem. 2011 76 3024.
doi: 10.1021/jo200509m |
[71] |
Quan Y. Xie Z. J. Am. Chem. Soc. 2014 136 15513.
doi: 10.1021/ja509557j |
[72] |
Kumar N. Bechtoldt A. Raghuvanshi K. Ackermann L. Angew. Chem., Int. Ed. 2016 55 6929.
doi: 10.1002/anie.201600490 |
[73] |
Zhang J. Shrestha R. Hartwig J. Zhao P. Nat. Chem. 2016 8 1144.
doi: 10.1038/nchem.2602 |
[74] |
Kim K. Vasu D. Im H. Hong S. Angew. Chem. Int. Ed. 2016 55 8652.
doi: 10.1002/anie.201603661 |
[75] |
Bhunia A. Studer A. ACS Catal. 2018 8 1213.
doi: 10.1021/acscatal.8b00083 |
[76] |
Kumar N. Rogge T. Yetra S. Bechtoldt A. Clot E. Ackermann L. Chem.-Eur. J. 2017 23 17449.
doi: 10.1002/chem.201703680 |
[77] |
Shi X. Liu K. Fan J. Dong X. Wei J. Li C. Chem.-Eur. J. 2015 21 1900.
doi: 10.1002/chem.201406031 |
[78] |
Tulichala R. Shankar M. Swamy K. J. Org. Chem. 2018 83 4375.
doi: 10.1021/acs.joc.8b00042 |
[79] |
Bhadra S. Dzik W. Gooßen L. Angew. Chem. Int. Ed. 2013 52 2959.
doi: 10.1002/anie.201208755 |
[80] |
Fu Z. Jiang Y. Wang S. Song Y. Guo S. Cai H. Org. Lett. 2019 21 3003.
doi: 10.1021/acs.orglett.9b00460 |
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