Progress in α-C(sp3)-H Arylation of Cyclic Compounds with Carbonyl Groups
- Corresponding author: Zhan Rui, sunnyzhanrui@126.com Shao Lidong, shaolidong@ynutcm.edu.cn
Citation:
Liu Yuanlie, Wang Mei, Chen Lei, Li Dashan, Wang Wenjing, Zhan Rui, Shao Lidong. Progress in α-C(sp3)-H Arylation of Cyclic Compounds with Carbonyl Groups[J]. Chemistry,
;2020, 83(7): 641-651.
Ren J, Shi X, Li X N, et al. Org. Lett., 2016, 18(16):3948~3951.
Zhu Y, Shao L D, Deng Z T, et al. J. Org. Chem., 2018, 83(17):10166~10174.
Xu J, Shao L D, Li D S, et al. J. Am. Chem. Soc., 2014, 136(52):17962~17965.
He J, Wasa M, Chan K S L, et al. Chem. Rev., 2017, 117(13):8754~8786.
Vargová D, Némethová L, Plevová K, et al. ACS Catal., 2019, 9(4):3104~3143.
Murahashi T, Kurosawa H. J. Organomet. Chem., 1999, 574(1):142~147.
Ciufolini M A, Qi H B, Browne M E. J. Org. Chem., 1988, 53(17):4149~4151.
Muratake H, Natsume M. Tetrahed. Lett., 1997, 38(43):7581~7582.
Palucki M, Buchwald S L. J. Am. Chem. Soc., 1997, 119(45):11108~11109.
Svennebring A, Garg N, Nilsson P, et al. J. Org. Chem., 2005, 70(12):4720~4725.
Storgaard M, Dörwald F Z, Peschke B, et al. J. Org. Chem., 2009, 74(14):5032~5040.
Bélanger É, Cantin K, Messe O, et al. J. Am. Chem. Soc., 2007, 129(5):1034~1035.
Solé D, Vallverdú L, Solans X, et al. J. Am. Chem. Soc., 2003, 125(6):1587~1594.
Huang Z, Chen Z L, Lim L H, et al. Angew. Chem. Int. Ed., 2013, 52(22):5807~5812.
hman J, Wolfe J P, Troustman M V, et al. J. Am. Chem. Soc., 1998, 120(8):1918~1919.
Kawatsura M, Hartwig J F. J. Am. Chem. Soc., 1999, 121(7):1473~1478.
Fox J M, Huang X H, Chieffi A, et al. J. Am. Chem. Soc., 2000, 122(7):1360~1370.
Ehrentraut A, Zapf A, Beller M. Adv. Synth. Catal., 2002, 344(2):209~217.
Liao X, Weng Z, Hartwig J F. J. Am. Chem. Soc., 2008, 130(1):195~200.
Viciu M S, Germaneau R F, Nolan S P. Org. Lett., 2002, 4(23):4053~4056.
Hamada T, Chieffi A, Åhman J, et al. J. Am. Chem. Soc., 2002, 124(7):1261~1268.
Liao X, Stanley L M, Hartwig J F. J. Am. Chem. Soc., 2011, 133(7):2088~2091.
Han C, Kim E H, Colby D A. J. Am. Chem. Soc., 2011, 133(15):5802~5805.
Jiao Z W, Beiger J J, Jin Y S, et al. J. Am. Chem. Soc., 2016, 138(49):15980~15986.
Shaughnessy K H, Hamann B C, Hartwig J F. J. Org. Chem., 1998, 63(19):6546~6553.
Altman R A, Hyde A M, Huang X H, et al. J. Am. Chem. Soc., 2008, 130(29):9613~9620.
Taylor A M, Altman R A, Buchwald S L. J. Am. Chem. Soc., 2009, 131(29):9900~9901.
Jin Y S, Chen M, Ge S Z, et al. Org. Lett., 2017, 19(6):1390~1393.
Xu Y, Su T S, Huang Z X, et al. Angew. Chem. Int. Ed., 2016, 55(7):2559~2563.
Liu R R, Li B L, Lu J, et al. J. Am. Chem. Soc., 2016, 138(16):5198~5201.
Zhu C D, Wang D Y, Sun W Y, et al. J. Am. Chem. Soc., 2017, 139(46):16486~16489.
Huang X, Oh W R J J, Zhou J S. Angew. Chem. Int. Ed., 2018, 57(26):7673~7677.
Wang M, Chen J, Chen Z J, et al. Angew. Chem. Int. Ed., 2018, 57(10):2707~2711.
Jiang L, Weist S, Jansat S. Org. Lett., 2009, 11(7):1543~1546.
Fernández-Nieto F, Mas Roselló J, Lenoir S, et al. Org. Lett., 2015, 17(15):3838~3841.
Hyde A M, Buchwald S L. Angew. Chem. Int. Ed., 2008, 47(1):177~180.
Zhao Y H, Zhou Y Y, Liang L L, et al. Org. Lett., 2009, 11(3):555~558.
Johnson T, Pultar F, Menke F, et al. Org. Lett., 2016, 18(24):6488~6491.
Yang Y C, Lin Y C, Wu Y K. Org. Lett., 2019, 21(23):9286~9290.
Semmelhack M F, Stauffer R D, Rogerson T D. Tetrahed. Lett., 1973, 14(45):4519~4522.
Spielvogel D J, Buchwald S L. J. Am. Chem. Soc., 2002, 124(14):3500~3501.
Chen G S, Kwong F Y, Chan H O, et al. Chem. Commun., 2006, (13):1413~1415.
Ge S, Hartwig J F. J. Am. Chem. Soc., 2011, 133(41):16330~16333.
Josep C, Jackson E P, Martin R. Angew. Chem. Int. Ed., 2015, 54(13):4075~4078.
Ghosh A, Walker J A, Arkady A, et al. ACS Catal., 2016, 6(4):2673~2680.
Harvey J S, Simonovich S P, Jamison C R, et al. J. Am. Chem. Soc., 2011, 133(35):13782~13785.
Liu T, Feng J J, Chen C, et al. Org. Lett., 2019, 21(12):4505~4509.
Baran P S, Richter J M. J. Am. Chem. Soc., 2004, 126(24):7450~7451.
Baran P S, Richter J M. J. Am. Chem. Soc., 2005, 127(44):15394~15396.
Baran P S, Maimone T J, Richter J M. Nature, 2007, 446(7134):404~408.
Wu H R, Huang H Y, Ren C L, et al. Chem. Eur. J., 2015, 21(47):16744~16748.
Guo J, Dong S X, Zhang Y L, et al. Angew. Chem. Int. Ed., 2013, 52(39):10245~10249.
Ueda N, Tokuyama T, Sakan T. Bull. Chem. Soc. Jpn., 1966, 39(9):2012~2014.
Stewart J D, Fields S C, Kochhar K S, et al. J. Org. Chem., 1987, 52(10):2110~2113.
Picazo E, Anthony S M, Giroud M, et al. J. Am. Chem. Soc., 2018, 140(24):7605~7610.
Semmelhack M F, Bargar T M. J. Org. Chem., 1977, 42(8):1481~1482.
Liang K, Li N, Zhang Y, et al. Chem. Sci., 2019, 10(10):3049~3053.
Shirakawa S, Koga K, Takuda T, et al. Angew. Chem. Int. Ed., 2014, 53(24):6220~6223.
Sattar M, Rathore V, Prasad C D, et al. Chem. Asian J., 2017, 12(7):734~743.
Rao X F, Li N K, Bai H, et al. Angew. Chem. Int. Ed., 2018, 57(38):12328~12332.
Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp3)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp3)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
Yujia Shi , Yan Qiao , Pengfei Xie , Miaomiao Tian , Xingwei Li , Junbiao Chang , Bingxian Liu . Rhodium-catalyzed enantioselective in situ C(sp3)−H heteroarylation by a desymmetrization approach. Chinese Chemical Letters, 2024, 35(10): 109544-. doi: 10.1016/j.cclet.2024.109544
Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp3)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
Lei Wan , Yizhou Tong , Xi Lu , Yao Fu . Cobalt-catalyzed reductive alkynylation to construct C(sp)-C(sp3) and C(sp)-C(sp2) bonds. Chinese Chemical Letters, 2024, 35(7): 109283-. doi: 10.1016/j.cclet.2023.109283
Jian Han , Li-Li Zeng , Qin-Yu Fei , Yan-Xiang Ge , Rong-Hui Huang , Fen-Er Chen . Recent advances in remote C(sp3)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction. Chinese Chemical Letters, 2024, 35(11): 109647-. doi: 10.1016/j.cclet.2024.109647
Jun Jiang , Hui Dai , Tao Tu . Two vicinal C(sp3)-F bonds functionalization of perfluoroalkyl halides (PFAHs). Chinese Chemical Letters, 2025, 36(7): 111054-. doi: 10.1016/j.cclet.2025.111054
Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By 1H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
Yajin Li , Huimin Liu , Lan Ma , Jiaxiong Liu , Dehua He . Photothermal Synthesis of Glycerol Carbonate via Glycerol Carbonylation with CO2 over Au/Co3O4-ZnO Catalyst. Acta Physico-Chimica Sinica, 2024, 40(9): 2308005-0. doi: 10.3866/PKU.WHXB202308005
Wei-Bin Li , Xiao-Chao Huang , Pei Liu , Jie Kong , Guo-Ping Yang . Recent advances in directing group assisted transition metal catalyzed para-selective C-H functionalization. Chinese Chemical Letters, 2025, 36(6): 110543-. doi: 10.1016/j.cclet.2024.110543
Hanxue LIU , Shijie LI , Meng REN , Xuling XUE , Hongke LIU . Design and antitumor properties of dehydroabietic acid functionalized cyclometalated iridium(Ⅲ) complex. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1483-1494. doi: 10.11862/CJIC.20250031
Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
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Yi Luo , Lin Dong . Multicomponent remote C(sp2)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
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