Rhodium-Catalyzed Dehydrogenative Cycloisomerization of Dienylcyclopropane to Highly Substituted Toluene

被引:2
|
作者
Nie, Wo [1 ]
Shen, Shichao [1 ]
Ma, Cheng [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
基金
中国国家自然科学基金;
关键词
METAL; CYCLOAROMATIZATION; CYCLOPROPANES; REARRANGEMENT; CYCLOADDITIONS; DERIVATIVES; ENEDIYNES; RINGS;
D O I
10.1021/acs.orglett.1c01265
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rhodium-catalyzed dehydrogenative cycloisomerization of dienylcyclopropane compounds is reported, which provides a straightforward approach to a variety of highly substituted toluene derivatives in 67-85% yields. The dienylcyclopropaneimides are produced by a single-step formal three-component olefination procedure. Preliminary mechanistic studies indicated that an electron-withdrawing group as R plays a critical role in completing this transformation.
引用
收藏
页码:4337 / 4341
页数:5
相关论文
共 50 条
  • [31] Rhodium-catalyzed approach to libraries of highly functionalized lactams
    Probst, DA
    Brummond, KM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3445 - U3445
  • [32] Novel rhodium-catalyzed cycloisomerization of 1,6-enynes with an intramolecular halogen shift
    Tong, XF
    Zhang, ZG
    Zhang, XM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (21) : 6370 - 6371
  • [33] Rhodium-Catalyzed Highly Enantioselective Hydrogenation of a Tetrasubstituted Enamine
    Yamada, Masatoshi
    Kato, Tomoaki
    Ikemoto, Tomomi
    Yamano, Mitsuhisa
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2021, 25 (04) : 1074 - 1079
  • [34] Novel rhodium-catalyzed cycloisomerization of 1,6-enynes with an intramolecular halogen shift
    Zhang, Z. (xumu@chem.psu.edu), 1600, American Chemical Society (125):
  • [35] Rhodium-Catalyzed Asymmetric Enyne Cycloisomerization of Terminal Alkynes and Formal Total Synthesis of (-)-Platensimycin
    Nicolaou, K. C.
    Li, Ang
    Ellery, Shelby P.
    Edmonds, David J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (34) : 6293 - 6295
  • [36] Highly enantioselective cycloisomerization of enynes catalyzed by rhodium for the preparation of functionalized lactams
    Lei, AW
    Waldkirch, JP
    He, MS
    Zhang, XM
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (23) : 4526 - +
  • [37] Rhodium-catalyzed asymmetric intramolecular cyclopropanation of substituted allylic cyanodiazoacetates
    Lin, W
    Charette, AB
    ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) : 1547 - 1552
  • [38] Rhodium-catalyzed carbonylative synthesis of silyl-substituted indenones
    Zhu, Fengxiang
    Spannenberg, Anke
    Wu, Xiao-Feng
    CHEMICAL COMMUNICATIONS, 2017, 53 (98) : 13149 - 13152
  • [39] Diversely Substituted Quinolines via Rhodium-Catalyzed Alkyne Hydroacylation
    Neuhaus, James D.
    Morrow, Sarah M.
    Brunavs, Michael
    Willis, Michael C.
    ORGANIC LETTERS, 2016, 18 (07) : 1562 - 1565
  • [40] Rhodium-Catalyzed Dehydrogenative Annulation of N-Arylmethanimines with Vinylene Carbonate for Synthesizing Quinolines
    Hu, Yan
    Nan, Jiang
    Yin, Jiacheng
    Huang, Guanjie
    Ren, Xin
    Ma, Yangmin
    ORGANIC LETTERS, 2021, 23 (21) : 8527 - 8532