Cascade Synthesis of 3-Alkylidene Dihydrobenzofuran Derivatives via Rhodium(III)-Catalyzed Redox-Neutral C-H Functionalization/Cyclization

被引：67
作者：
Zhou, Zhi [1 ]
Liu, Guixia [1 ]
Chen, Yan [1 ]
Lu, Xiyan [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 23期
基金：
中国国家自然科学基金;
关键词：
N-PHENOXYACETAMIDES; INDOLE SYNTHESIS; ACTIVATION; BOND; ALKYNES; MILD; ANNULATION; ACCESS; ARYLNITRONES; CONSTRUCTION;
D O I：
10.1021/acs.orglett.5b03060
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient rhodium(III)-catalyzed coupling reaction of N-phenoxyacetamides with propargyl carbonates to yield 3-alkylidene dihydrobenzofuran derivatives via C-H functionalization/cascade cyclization has been developed. This transformation represents a redox-neutral process and features the formation of three new bonds under mild conditions.
引用
收藏
页码：5874 / 5877
页数：4
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    Dai, Lu
    Shao, Xiaoru
    Hong, Mei
    Zhao, Jing
    Huang, Yong
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  • [2] Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions
    Colby, Denise A.
    Tsai, Andy S.
    Bergman, Robert G.
    Ellman, Jonathan A.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) : 814 - 825
  • [3] Selective Cyclization of Arylnitrones to Indolines under External Oxidant-Free Conditions: Dual Role of Rh(III) Catalyst in the C-H Activation and Oxygen Atom Transfer
    Dateer, Ramesh B.
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    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (15) : 4908 - 4911
  • [4] Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon-Hydrogen Bonds
    Daugulis, Olafs
    Roane, James
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    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (04) : 1053 - 1064
  • [5] RhIII-Catalyzed Redox-Neutral C-H Activation of Pyrazolones: An Economical Approach for the Synthesis of N-Substituted Indoles
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    Song, Shanshan
    Li, Wei
    Geng, Kaijun
    Xu, Youjun
    Miao, Ze-Hong
    Zhang, Ao
    [J]. ORGANIC LETTERS, 2015, 17 (02) : 310 - 313
  • [6] Low-Valent Cobalt Catalysis: New Opportunities for C-H Functionalization
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    Yoshikai, Naohiko
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (04) : 1208 - 1219
  • [7] The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations
    Girard, Simon A.
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    Li, Chao-Jun
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) : 74 - 100
  • [8] Rhodium(III)-Catalyzed Heterocycle Synthesis Using an Internal Oxidant: Improved Reactivity and Mechanistic Studies
    Guimond, Nicolas
    Gorelsky, Serge I.
    Fagnou, Keith
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (16) : 6449 - 6457
  • [9] Rhodium(III)-Catalyzed Isoquinolone Synthesis: The N-O Bond as a Handle for C-N Bond Formation and Catalyst Turnover
    Guimond, Nicolas
    Gouliaras, Christina
    Fagnou, Keith
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (20) : 6908 - +
  • [10] Rhodium(III)-Catalyzed ortho Alkenylation of N-Phenoxyacetamides with N-Tosylhydrazones or Diazoesters through C-H Activation
    Hu, Fangdong
    Xia, Ying
    Ye, Fei
    Liu, Zhenxing
    Ma, Chen
    Zhang, Yan
    Wang, Jianbo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (05) : 1364 - 1367
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