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Issue 4, 2017

Highly chemoselective ruthenium(ii)-catalyzed direct arylation of cyclic and N,N-dialkyl benzamides with aryl silanes

Author affiliations

Abstract

The ruthenium(II)-catalyzed oxidative cross-coupling of C(sp2)–H bonds with organosilanes has been accomplished for the first time. This novel protocol enlists challenging cyclic and N,N-dialkyl benzamides as weakly-coordinating substrates to achieve highly regioselective C(sp2)–H arylation as a proof-of-concept, taking advantage of the attractive features of organosilanes as coupling partners. This innovative method is characterized by very high chemoselectivity, installing halide functional groups (I, Br, Cl) that are incompatible with Ru(II)-carboxylate systems employing halides as cross-coupling partners, while obviating the need for sensitive organometallic reagents and cryogenic temperatures typical to the classic directed-ortho-metallation (DoM) techniques, employing benzamides to afford bioactive structural motifs.

Graphical abstract: Highly chemoselective ruthenium(ii)-catalyzed direct arylation of cyclic and N,N-dialkyl benzamides with aryl silanes

Supplementary files

Article information


Submitted
12 Jan 2017
Accepted
16 Feb 2017
First published
24 Feb 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 3204-3210
Article type
Edge Article

Highly chemoselective ruthenium(II)-catalyzed direct arylation of cyclic and N,N-dialkyl benzamides with aryl silanes

P. Nareddy, F. Jordan and M. Szostak, Chem. Sci., 2017, 8, 3204 DOI: 10.1039/C7SC00156H

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