Lewis Acid/Brønsted Acid Controlled Pd(II)-Catalyzed Chemodivergent Functionalization of C( sp2 )-H Bonds with N-(Arylthio)i(a)mides

Organic Letters
Manthena Chaitanya, Pazhamalai Anbarasan

Abstract

An efficient and chemodivergent palladium-catalyzed thiolation (C-S) and imidation (C-N) of directing group-assisted C-H bonds have been accomplished employing N-(arylthio)imides in combination with either Brønsted acid or Lewis acid, respectively. Notable features of the developed methodologies include excellent diversity, high functional group tolerance, wide substrate scope, and use of a single N-S reagent. Importantly, the developed hypothesis was also successfully extended to the amidation of C-H bonds. A plausible mechanistic pathway was proposed based on the preliminary mechanistic study.

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Citations

Jan 19, 2019·Chemical Communications : Chem Comm·Fan LvLijuan Jiao
Feb 23, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Koji YamamotoToshikazu Takata
May 1, 2020·Chemistry, an Asian Journal·Seiya KataharaNoritaka Chida

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