Vinylation of aldehydes using Mn/Cr alloy and a N4 -ligand/Ni(II) -catalyst

Chemistry : a European Journal
Wacharee Harnying, Albrecht Berkessel

Abstract

We report an efficient and practical protocol for the Cr/Ni-catalyzed vinylation of aldehydes, based on the use of Mn/Cr alloy (ca. 10 % Cr) and TMSCl. No additional Cr salts need to be added. In the presence of NiCl2 (0.3 mol %) and a bis(ketimino)-2,2'-bipyridine as N4 -chelating ligand (1 mol %), the vinylations proceed smoothly at room temperature. The presence of catalytic amounts of MeOH and LiOAc as additives was found to further promote the efficiency of the catalytic system, even in the absence of the ligand. Detailed reaction monitoring revealed that LiOAc accelerates the product alcohol silylation, thus increasing the turnover rate.

References

Dec 6, 2002·Organic Letters·Hyeong-Wook ChoiYoshito Kishi
Apr 9, 2004·Organic Letters·Ian PatersonAlbrecht Berkessel
Apr 24, 2004·The Journal of Organic Chemistry·Albrecht BerkesselJörg M Neudörfl
Dec 21, 2004·Organic Letters·Kosuke Namba, Yoshito Kishi
Nov 18, 2005·Organic Letters·Kosuke NambaYoshito Kishi
Jun 20, 2008·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Masahiro InoueMasahisa Nakada
Dec 17, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Gerry A GriffithGregory A Solan
Oct 3, 2009·Journal of the American Chemical Society·Haibing GuoYoshito Kishi
Mar 23, 2011·Chemistry : a European Journal·Wacharee HarnyingAlbrecht Berkessel
Mar 27, 2012·Journal of the American Chemical Society·Xiang LiuYoshito Kishi

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Citations

Sep 11, 2020·Journal of the American Chemical Society·Marino BörjessonRuben Martin

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