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

Chemical Science
Pradeep NareddyMichal Szostak

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.

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Citations

Jul 22, 2020·Organic & Biomolecular Chemistry·Writhabrata SarkarIndubhusan Deb
Jan 20, 2021·Organic Letters·Ravichandran Logeswaran, Masilamani Jeganmohan
Apr 24, 2021·Organic & Biomolecular Chemistry·Xin-Xing WuLanping Hu
Jun 2, 2021·Organic Letters·Chikkabagilu Nagaraju Shambhavi, Masilamani Jeganmohan
Jun 3, 2021·Organic & Biomolecular Chemistry·Ruchi Sharma, M Ramu Yadav
Mar 2, 2019·The Journal of Organic Chemistry·Ramakrishnan SivasakthikumaranMasilamani Jeganmohan
Mar 3, 2018·The Journal of Organic Chemistry·Masilamani TamizmaniMasilamani Jeganmohan
Dec 29, 2017·Organic Letters·Pradeep NareddyMichal Szostak
Nov 1, 2017·The Journal of Organic Chemistry·Nagnath Yadav MoreMasilamani Jeganmohan
Nov 11, 2017·The Journal of Organic Chemistry·Kun JingGuan-Wu Wang
May 26, 2018·The Journal of Organic Chemistry·Adapa AnukumarMasilamani Jeganmohan
Sep 24, 2021·Organic & Biomolecular Chemistry·Zixian YangChangduo Pan

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