Cu-Catalyzed Direct C-H Alkylation of Polyfluoroarenes via Remote C(sp)-H Functionalization in Carboxamides.

Org Lett

State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P.R. China.

Published: April 2021


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Article Abstract

A novel dehydrogenative coupling reaction of -fluorocarboxamides with polyfluoroarenes forming C(sp)-C(sp) bonds enabled by copper catalysis has been accomplished. -Fluorocarboxamides are postulated to undergo copper-mediated dehydrogenative cross-coupling reaction with electron-deficient polyfluoroarenes via a radical pathway. Benzylic C-H bonds and aliphatic C-H bonds in -fluorocarboxamides could proceed smoothly and demonstrated excellent regioselectivity. The detailed mechanism presented is supported by control experiments and density functional theory calculations.

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http://dx.doi.org/10.1021/acs.orglett.1c00586DOI Listing

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