Progress in Diazo Compounds Mediated Transition-Metal-Catalyzed C-H Alkylation

被引:14
|
作者
Wang, Liang [1 ]
Li, Zhan [1 ]
Wan, Kang [1 ]
Qu, Xing [1 ]
Hu, Siqian [1 ]
Wang, Feng [2 ]
机构
[1] Jianghan Univ, Sch Chem & Environm Engn, Minist Educ, Key Lab Optoelect Chem Mat & Devices, Wuhan 430056, Peoples R China
[2] Hubei Engn Univ, Coll Chem & Mat Sci, Xiaogan 432000, Peoples R China
基金
中国国家自然科学基金;
关键词
diazo compounds; transition-metal-catalysis; C-H activation; alkyaltion; N BOND FORMATION; FACILE SYNTHESIS; CARBENOID FUNCTIONALIZATION; RH(III)-CATALYZED SYNTHESIS; REGIOSELECTIVE SYNTHESIS; ROOM-TEMPERATURE; ACTIVATION; INDOLES; DERIVATIVES; COPPER;
D O I
10.6023/cjoc201511017
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diazo compounds had been widely employed as a class of environment friendly and highly efficient coupling reagents in transition-metal-catalyzed C-H bonds insertion reactions. Recently, C-H alkylation of various arenes and heteroarenes has been achieved enormous successes using diazo compounds as the alkylation reagents under a new catalytic model. The recent progress in diazo compounds mediated transition-metal-catalyzed C-H alkylation and tandem C-H alkylation/cyclization is reviewed, including reaction mechanism and synthetic applications. Furthermore, the prospects of this reaction are also discussed.
引用
收藏
页码:889 / 912
页数:24
相关论文
共 108 条
  • [1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations
    Ackermann, Lutz
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) : 281 - 295
  • [2] Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond cleavages with unactivated alkyl halides
    Ackermann, Lutz
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (27) : 4866 - 4877
  • [3] Rhodium(III)- and Iridium(III)-Catalyzed C7 Alkylation of Indolines with Diazo Compounds
    Ai, Wen
    Yang, Xueyan
    Wu, Yunxiang
    Wang, Xuan
    Li, Yuanchao
    Yang, Yaxi
    Zhou, Bing
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (52) : 17653 - 17657
  • [4] The bohimann-rahtz pyridine synthesis: From discovery to applications
    Bagley, Mark C.
    Glover, Christian
    Merritt, Eleanor A.
    [J]. SYNLETT, 2007, (16) : 2459 - 2482
  • [5] Catalytic Functionalization of Indoles in a New Dimension
    Bandini, Marco
    Eichholzer, Astrid
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) : 9608 - 9644
  • [6] Synthesis and functionalization of Indoles through palladium-catalyzed reactions
    Cacchi, S
    Fabrizi, G
    [J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2873 - 2920
  • [7] Rh-Catalyzed Intermolecular Carbenoid Functionalization of Aromatic C-H Bonds by α-Diazomalonates
    Chan, Wai-Wing
    Lo, Siu-Fung
    Zhou, Zhongyuan
    Yu, Wing-Yiu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) : 13565 - 13568
  • [8] Chen B, 2000, CHINESE J ORG CHEM, V20, P433
  • [9] Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter
    Chen, X
    Li, JJ
    Hao, XS
    Goodhue, CE
    Yu, JQ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) : 78 - 79
  • [10] Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids:: Two distinct C-H activation pathways
    Chen, Xiao
    Goodhue, Charles E.
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12634 - 12635