Palladium(II)-catalyzed aerobic hydroalkoxylation of styrenes containing a phenol

Journal of the American Chemical Society
Keith M GligorichMatthew S Sigman

Abstract

An intermolecular Pd-catalyzed hydroalkoxylation of styrenes that contain a phenol is presented. The reaction can be performed on terminal, disubstituted, and trisubstituted olefins in a variety of alcoholic solvents. Initial mechanistic data suggest a mechanism that involves oxidation of the alcoholic solvent to provide a Pd-hydride that inserts into an olefin. This is followed by formation of a quinone methide and subsequent addition of an alcohol to yield the hydroalkoxylated product.

References

Jan 25, 2005·Angewandte Chemie·Ian PatersonAngela C Mackay

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Citations

Nov 19, 2010·Journal of the American Chemical Society·Katrina H JensenMatthew S Sigman
Oct 18, 2011·The Journal of Organic Chemistry·Tejas P Pathak, Matthew S Sigman
May 21, 2010·Organic Letters·Erik W WernerMatthew S Sigman
Apr 23, 2011·Organic Letters·Tejas P Pathak, Matthew S Sigman
Aug 31, 2007·Chemical Communications : Chem Comm·Cong LiuRoss A Widenhoefer
Jun 13, 2009·Chemical Communications : Chem Comm·Takahiro KawamotoTamio Hayashi
Aug 8, 2009·Chemical Communications : Chem Comm·Keith M Gligorich, Matthew S Sigman
Jul 9, 2016·Organic Letters·Lun XuYu-Ming Zhao
Feb 21, 2014·Angewandte Chemie·Barry M Trost, Lara C Czabaniuk
Apr 4, 2008·Organic & Biomolecular Chemistry·Jiajing TanZhiyong Wang
Mar 5, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Antonio G De CrisciUlrich Fekl
Feb 24, 2012·Chemical Society Reviews·Zhuangzhi ShiNing Jiao
May 6, 2017·Physical Chemistry Chemical Physics : PCCP·Alberto LesarriMarco A Gigosos
Dec 23, 2020·Angewandte Chemie·Goki HirataTakashi Nishikata
Nov 2, 2007·Chemical Reviews·Egle M BeccalliSilvia Sottocornola
Aug 25, 2006·Organic Letters·Candace N Cornell, Matthew S Sigman
Sep 4, 2009·Organic Letters·Frédéric LironGiovanni Poli
Nov 22, 2013·Journal of the American Chemical Society·Yinjun XieHanmin Huang
May 21, 2015·Chemical Reviews·Mohammad HassamWillem A L van Otterlo
Dec 5, 2012·Journal of the American Chemical Society·Yi Luan, Scott E Schaus
May 6, 2015·Organic Letters·Michael W DannemanJeffrey N Johnston
May 17, 2014·Journal of the American Chemical Society·Ying DuanYong-Gui Zhou
Jul 4, 2013·Journal of the American Chemical Society·Hiroki ShigehisaKou Hiroya
Oct 30, 2007·Journal of the American Chemical Society·Keith M GligorichMatthew S Sigman

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