Pd-catalyzed asymmetric Suzuki-Miyaura coupling reactions for the synthesis of chiral biaryl compounds with a large steric substituent at the 2-position.

Beilstein Journal of Organic Chemistry
Yongsu LiLiqin Qiu

Abstract

Pd-catalyzed asymmetric Suzuki-Miyaura couplings of 3-methyl-2-bromophenylamides, 3-methyl-2-bromo-1-nitrobenzene and 1-naphthaleneboronic acids have been successfully developed and the corresponding axially chiral biaryl compounds were obtained in very high yields (up to 99%) with good enantioselectivities (up to 88% ee) under mild conditions. The chiral-bridged biphenyl monophosphine ligands developed by our group exhibit significant superiority to the naphthyl counterpart MOP in both reactivity and enantioselectivity control. The large steric hindrance from π-conjugated ortho-substituents of the bromobenzene substrates and the Pd···O interaction between carbonyl and palladium seem essential to achieve high enantioselectivity.

References

May 9, 2002·Chemical Reviews·Jwanro HassanMarc Lemaire
Oct 16, 2002·Accounts of Chemical Research·Scott E Denmark, Ramzi F Sweis
Feb 22, 2003·Angewandte Chemie·Brian K Hubbard, Christopher T Walsh
Jun 5, 2004·The Journal of Organic Chemistry·Takashi WatanabeMotokazu Uemura
Aug 24, 2005·Angewandte Chemie·Gerhard BringmannMatthias Breuning
Jul 16, 2008·Accounts of Chemical Research·Ruben Martin, Stephen L Buchwald
Nov 5, 2008·Journal of the American Chemical Society·Antonio BermejoJosé M Lassaletta
Jul 29, 2009·Angewandte Chemie·Jonathan ClaydenSteven R LaPlante
Oct 23, 2009·Chemical Society Reviews·Marisa C KozlowskiElizabeth C Linton
Sep 14, 2010·Journal of the American Chemical Society·Hiromichi EgamiTsutomu Katsuki
Oct 14, 2010·Chemical Reviews·Gerhard BringmannMatthias Breuning
Aug 19, 2011·Journal of Medicinal Chemistry·Steven R LaplantePaul J Edwards
Apr 14, 2012·Organic Letters·Wenjun TangChris H Senanayake
Apr 19, 2012·The Journal of Organic Chemistry·Abel RosJosé M Lassaletta
Jan 9, 2013·Chemistry : a European Journal·Qing ZhaoWenjun Tang
Feb 16, 2013·Journal of the American Chemical Society·Kimberly T Barrett, Scott J Miller
Oct 11, 2013·Journal of the American Chemical Society·Abel RosJosé M Lassaletta
Oct 24, 2013·Journal of the American Chemical Society·Guangqing XuWenjun Tang
Oct 25, 2013·Journal of the American Chemical Society·Vikram BhatScott C Virgil
Apr 24, 2015·Chemical Society Reviews·J Wencel-DelordF Colobert
Aug 19, 2015·Natural Product Reports·Jamie E SmythPaul A Keller
Nov 13, 2015·Journal of the American Chemical Society·Ye-Hui ChenBin Tan
Dec 12, 2019·Chemical Science·Seoung-Tae KimMu-Hyun Baik

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Methods Mentioned

BETA
column chromatography
NMR

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