Issue 13, 2017

Palladium-catalyzed interannular meta-C–H arylation

Abstract

The interannular meta-selective C–H arylation of biaryl-2-trifluoroacetamides using Pd(II)/norbornene catalysis is reported. The installation of a trifluoroacetyl protecting group to tune their electronic properties and binding ability is essential for interannular selectivity. A dimeric palladacycle, comprising two cyclopalladated trifluoroacetamino biaryl units linked through trifluoroacetamide, was isolated and confirmed to be the key intermediate. Furthermore, the resulting products could be further elaborated via ipso-alkynylation and/or directed intraannular ortho-C–H functionalization, allowing access to various fully functionalized biaryl-2-amine derivatives.

Graphical abstract: Palladium-catalyzed interannular meta-C–H arylation

Supplementary files

Article information

Article type
Communication
Submitted
06 Jan 2017
Accepted
20 Jan 2017
First published
23 Jan 2017

Chem. Commun., 2017,53, 2166-2169

Palladium-catalyzed interannular meta-C–H arylation

P. Ling, K. Chen and B. Shi, Chem. Commun., 2017, 53, 2166 DOI: 10.1039/C7CC00110J

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