A Direct Access to 7-Aminoindoles via Iridium-Catalyzed Mild C–H Amidation of N-Pivaloylindoles with Organic Azides - Organic Letters (ACS Publications)

A Direct Access to 7-Aminoindoles via Iridium-Catalyzed Mild C–H Amidation of N-Pivaloylindoles with Organic Azides - Organic Letters (ACS Publications)

A Direct Access to 7-Aminoindoles via Iridium-Catalyzed Mild C–H Amidation of N-Pivaloylindoles with Organic Azides

Youyoung Kim^†‡, Juhyeon Park^†‡, and Sukbok Chang^*‡†

^† Department
of Chemistry, Korea Advanced Institute of
Science and Technology (KAIST), Daejeon 305-701, Korea

^‡ Center
for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 305-701, Korea

Org. Lett., Article ASAP

DOI: 10.1021/acs.orglett.6b00662

Publication Date (Web): March 29, 2016

Copyright © 2016 American Chemical Society

*E-mail: sbchang@kaist.ac.kr.

Abstract

Ir(III)-catalyzed
regioselective direct C-7 amidation of indoles in reaction with organic
azides has been developed. While its efficiency was varied by the
choice of N-directing groups, N-pivaloylindoles were most
effective in undergoing the desired amidation at room temperature over a
broad range of substrates. The reaction was scalable, and deprotection
of the chelation group was also facile.