Rhodium(III)-catalyzed intermolecular cyclization of anilines with sulfoxonium ylides toward indoles

C2-substituted indoles were efficiently prepared with excellent regio-selectivity from N-phenylpyridin-2-amines and sulfoxonium ylides via cascade reaction of C–H alkylation/nucleophilic cyclization. [Display omitted] Rhodium(III)-catalyzed synthesis of indole derivatives has been realized via casca...

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Published inChinese chemical letters Vol. 30; no. 7; pp. 1374 - 1378
Main Authors Shen, Zhihao, Pi, Chao, Cui, Xiuling, Wu, Yangjie
Format Journal Article
LanguageEnglish
Published NEW YORK Elsevier B.V 01.07.2019
Elsevier
Department of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities,Zhengzhou University, Zhengzhou 450052, China
Subjects
Aniline
Chemistry
Chemistry, Multidisciplinary
Cyclization
Indole
Physical Sciences
Rhodium
Science & Technology
Sulfoxonium ylide
Rhodium
Cyclization
Aniline
Indole
Sulfoxonium ylide
FUNCTIONALIZATIONS
ANNULATION
NATURAL-PRODUCTS
ALKYNES
N-(2-PYRIDYL)INDOLES
C-H ACTIVATION
DERIVATIVES
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Summary:C2-substituted indoles were efficiently prepared with excellent regio-selectivity from N-phenylpyridin-2-amines and sulfoxonium ylides via cascade reaction of C–H alkylation/nucleophilic cyclization. [Display omitted] Rhodium(III)-catalyzed synthesis of indole derivatives has been realized via cascade reaction of CH alkylation/nucleophilic cyclization starting from readily available N-phenylpyridin-2-amines and sulfoxonium ylides. Notably, this transformation could smoothly proceed with high yields, good regioselectivity, and feature broad group tolerance and under redox-neutral condition to avoid external oxidant. The titled products are potentially important building blocks in the organic synthesis through various chemical transformations.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2019.01.033