Rhodium-Catalyzed sp 2 C-H Acetoxylation of N-Aryl Azaindoles/N-Heteroaryl Indolines

A silver- and copper-free rhodium-catalyzed C-H acetoxylation reaction of azaindoles has been achieved at near ambient temperature employing PIDA as a nonmetallic acetoxy source. The method is highly selective, efficient, and scalable and requires acetic anhydride as the sole additive. The scope of...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-12, Vol.82 (23), p.12406-12415
Main Authors: Mishra, Aniket, Vats, Tripta Kumari, Nair, Mahesh P, Das, Arindam, Deb, Indubhusan
Format: Article
Language:English
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Summary:A silver- and copper-free rhodium-catalyzed C-H acetoxylation reaction of azaindoles has been achieved at near ambient temperature employing PIDA as a nonmetallic acetoxy source. The method is highly selective, efficient, and scalable and requires acetic anhydride as the sole additive. The scope of the reaction has been successfully tested with a wide array of medicinally important heterocyclic scaffolds with diverse functional group tolerance. A series of kinetic experiments was conducted to gain detailed insight into the reaction mechanism. The methodology developed could be successfully expanded for C7-acetoxylation of indoline derivatives using pyrimidine as a detachable directing group for the synthesis of 7-hydroxyindole.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02203