N-Heterocyclic Carbene-Catalyzed Conjugate Additions of Alcohols

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 ca...

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Bibliographic Details
Published in:	Journal of the American Chemical Society 2010-09, Vol.132 (38), p.13179-13181
Main Authors:	Phillips, Eric M, Riedrich, Matthias, Scheidt, Karl A
Format:	Article
Language:	eng
Subjects:	Alcohols - chemistry Catalysis Heterocyclic Compounds - chemistry Methane - analogs & derivatives Methane - chemistry
Online Access:	Get full text
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Summary:	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.
ISSN:	0002-7863 1520-5126