Issue 4, 2017

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

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

Article type
Edge Article
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
Creative Commons BY-NC license

Chem. Sci., 2017,8, 3204-3210

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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