Rhodium-catalyzed cycloisomerization: Formation of indoles, benzofurans, and enol lactones

被引：174
|
作者：
Trost, Barry M. [1 ]
McClory, Andrew [1 ]
机构：
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 12期
关键词：
alkynes; atom economy; cyclization; homogeneous catalysis; rhodium; BIS-HOMOPROPARGYLIC ALCOHOLS; METAL VINYLIDENE CARBENES; 2-ETHYNYLANILINE DERIVATIVES; RECONSTITUTIVE CONDENSATION; 2-SUBSTITUTED INDOLES; TERMINAL ALKYNES; ATOM ECONOMY; ALLYL ALCOHOLS; CYCLIZATION; 2-ALKYNYLANILINES;
D O I：
10.1002/anie.200604183
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Internal affairs: Indoles, benzofurans, and enol lactones are formed chemoselectively from the rhodium-catalyzed cyclo-isomerization reaction of easily prepared alkynyl aniline substrates (see scheme, cod = cycloocta-1,5-diene, DMF = N,N-dimethylformamide). The reaction may proceed by nucleophilic capture of a vinylidene intermediate. Indoles are formed under mild conditions using low catalyst loadings. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：2074 / 2077
页数：4
相关论文
共 50 条
  • [1] Rhodium-Catalyzed Intermolecular Cyclopropanation of Benzofurans, Indoles, and Alkenes via Cyclopropene Ring Opening
    Ross, Rachel J.
    Jeyaseelan, Rubaishan
    Lautens, Mark
    ORGANIC LETTERS, 2020, 22 (12) : 4838 - 4843
  • [2] Rhodium-catalyzed cycloisomerization of allenenes via metalacycle intermediates
    Makino, T
    Itoh, K
    TETRAHEDRON LETTERS, 2003, 44 (33) : 6335 - 6338
  • [3] Rhodium-Catalyzed Dehydrogenative Cycloisomerization of Dienylcyclopropane to Highly Substituted Toluene
    Nie, Wo
    Shen, Shichao
    Ma, Cheng
    ORGANIC LETTERS, 2021, 23 (11) : 4337 - 4341
  • [4] Rhodium-catalyzed cycloisomerization of N-propargyl enamine derivatives
    Kim, Hahn
    Lee, Chulbom
    Journal of the American Chemical Society, 2006, 128 (19): : 6336 - 6337
  • [5] A rhodium-catalyzed C-H activation/cycloisomerization tandem
    Aissa, Christophe
    Fuerstner, Alois
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (48) : 14836 - +
  • [6] Rhodium-catalyzed cycloisomerization of N-propargyl enamine derivatives
    Kim, Hahn
    Lee, Chulbom
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (19) : 6336 - 6337
  • [7] A rhodium-catalyzed C-H activation/cycloisomerization tandem
    Aissa, Christophe
    Furstner, Alois
    1600, American Chemical Society, Columbus, OH 43210-3337, United States (129):
  • [8] Rhodium-catalyzed asymmetric [4+2] cycloisomerization reactions
    Gilbertson, SR
    Hoge, GS
    Genov, DG
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26): : 10077 - 10080
  • [9] Rhodium-Catalyzed Intermolecular Stereoselective Allylation of Indoles with Allenes
    Ma, Chaoyan
    Li, Can
    Bai, Jiahui
    Xiao, Junzhe
    Zhai, Yizhan
    Guo, Yinlong
    Ma, Shengming
    ACS CATALYSIS, 2022, 12 (16) : 10141 - 10146
  • [10] Rhodium-Catalyzed [3+2] Annulation of Indoles
    Lian, Yajing
    Davies, Huw M. L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (02) : 440 - +
12345