3 years ago

Rhodium-Catalyzed sp2 C–H Acetoxylation of N-Aryl Azaindoles/N-Heteroaryl Indolines

Rhodium-Catalyzed sp2 C–H Acetoxylation of N-Aryl Azaindoles/N-Heteroaryl Indolines
Aniket Mishra, Mahesh P. Nair, Arindam Das, Indubhusan Deb, Tripta Kumari Vats
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02203

DOI: 10.1021/acs.joc.7b02203

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