NHC ligand-powered palladium-catalyzed carbonylative C-S bond cleavage of vinyl sulfides: efficient access to tert-butyl arylacrylates

被引：2
作者：
Xu, Jian-Xing [1 ]
Zhao, Fengqian [2 ]
Wu, Xiao-Feng [1 ,2 ]
机构：
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian Natl Lab Clean Energy, Dalian 116023, Liaoning, Peoples R China
[2] Univ Rostock, Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 48期
关键词：
CARBON-MONOXIDE; CONJUGATE ADDITION; COMPLEXES; ESTERS; TRANSFORMATION; ACTIVATION; KETONES; AMINES;
D O I：
10.1039/d0ob02043e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A method for palladium-catalyzed carbonylative C-S bond activation of divinyl sulfides to synthesize numerous tert-(E)-butyl arylacry-lates under 1 bar of CO has been developed. Employing electron-rich NHC as the ligand, the electron-rich and stabilized palladium complex trend to oxidative addition to the relatively inert C-S bond and decreased the poisoning effect of sulfide and CO; a series of tert-(E)-butyl acrylates were obtained in moderate to good yields.
引用
收藏
页码：9796 / 9799
页数：4
相关论文
共 51 条
  • [41] Efficient cleavage of carboxylic tert-butyl and 1-adamantyl esters, and N-Boc-amines using H2SO4 in CH2Cl2
    Strazzolini, P
    Misuri, N
    Polese, P
    [J]. TETRAHEDRON LETTERS, 2005, 46 (12) : 2075 - 2078
  • [42] DIASTEREOSELECTIVE SYNTHESIS OF BICYCLOPROPANES
    THEBERGE, CR
    ZERCHER, CK
    [J]. TETRAHEDRON LETTERS, 1994, 35 (49) : 9181 - 9184
  • [43] The Development of Bulky Palladium NHC Complexes for the Most-Challenging Cross-Coupling Reactions
    Valente, Cory
    Calimsiz, Selcuk
    Hoi, Ka Hou
    Mallik, Debasis
    Sayah, Mahmoud
    Organ, Michael G.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (14) : 3314 - 3332
  • [44] Palladium-Catalyzed Carbonylative Transformation of C(sp3)-X Bonds
    Wu, Lipeng
    Fang, Xianjie
    Liu, Qiang
    Jackstell, Ralf
    Beller, Matthias
    Wu, Xiao-Feng
    [J]. ACS CATALYSIS, 2014, 4 (09): : 2977 - 2989
  • [45] A practical chlorination of tert-butyl esters with PCl3 generating acid chlorides
    Wu, Xiaofang
    Zhou, Lei
    Yang, Ruoqi
    Guo, Fengzhe
    Tang, Zi-Long
    Xiao, Jing
    [J]. JOURNAL OF CHEMICAL RESEARCH, 2020, 44 (5-6) : 301 - 304
  • [46] Ruthenium-Catalyzed Carbonylative Coupling of Anilines with Organoboranes by the Cleavage of Neutral Aryl C-N Bond
    Xu, Jian-Xing
    Zhao, Fengqian
    Yuan, Yang
    Wu, Xiao-Feng
    [J]. ORGANIC LETTERS, 2020, 22 (07) : 2756 - 2760
  • [47] Yadav YS, 2002, SYNLETT, P826
  • [48] No Making Without Breaking: Nitrogen-Centered Carbonylation Reactions
    Yin, Zhiping
    Xu, Jianxing
    Wu, Xiao-Feng
    [J]. ACS CATALYSIS, 2020, 10 (11) : 6510 - 6531
  • [49] Transition-Metal-Free Alkoxycarbonylation of Aryl Halides
    Zhang, Hua
    Shi, Renyi
    Ding, Anxing
    Lu, Lijun
    Chen, Borui
    Lei, Aiwen
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (50) : 12542 - 12545
  • [50] N-Heterocyclic Carbene Complexes in C-H Activation Reactions
    Zhao, Qun
    Meng, Guangrong
    Nolan, Steven P.
    Szostak, Michal
    [J]. CHEMICAL REVIEWS, 2020, 120 (04) : 1981 - 2048
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