<i>N</i>-Heterocyclic Carbene-Catalyzed Conjugate Additions of Alcohols
Journal of the American Chemical SocietyPublished 1 September 2010
Eric M. Phillips, Matthias Riedrich, Karl A. Scheidt
Citations212
SJR quartileQ1
SJR score5.55
SNIP2.61
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TL;DR
An efficient intermolecular conjugate addition of alcohols to activated alkenes catalyzed by N-heterocyclic carbenes has been developed and preliminary data support a Brønsted base mechanism with the free carbene.
Abstract
An efficient intermolecular conjugate addition of alcohols to activated alkenes catalyzed by N-heterocyclic carbenes has been developed. With 5 mol % of the free carbene derived from IMes·HCl, unsaturated ketones and esters are competent substrates, and a variety of primary and secondary alcohols can be employed as the nucleophile. No oligomerization is observed under these mild conditions for effective hydroalkoxylation. In addition to reactions with activated alkenes, IMes catalyzes the formation of vinyl ethers through the 1,4-addition of alcohols to ynones and promotes tandem conjugate addition/Michael cascade reactions. Preliminary data support a Brønsted base mechanism with the free carbene.
Keywords
Chemistry
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