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A [4+1] Cyclative Capture Approach to 3 H ‐Indole‐ N ‐oxides at Room Temperature by Rhodium(III)‐Catalyzed CH Activation
Author(s) -
Yang Yaxi,
Wang Xuan,
Li Yuanchao,
Zhou Bing
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201508702
Subject(s) - rhodium , indole test , aniline , catalysis , chemistry , diazo , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry
The rhodium(III)‐catalyzed [3+2] CH cyclization of aniline derivatives and internal alkynes represents a useful contribution to straightforward synthesis of indoles. However, there is no report on the more challenging synthesis of pharmaceutically important N ‐hydroxyindoles and 3 H ‐indole‐ N ‐oxides. Reported herein is the first rhodium(III)‐catalyzed [4+1] CH oxidative cyclization of nitrones with diazo compounds to access 3 H ‐indole‐ N ‐oxides. More significantly, this reaction proceeds at room temperature and has been extended to the synthesis of N ‐hydroxyindoles and N ‐hydroxyindolines.