title: N-heterocyclic carbene-catalyzed conjugate additions of alcohols.
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.
authors.affiliation: Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, Silverman Hall, 2145 Sheridan Road, Evanston, Illinois 60208, USA.
authors.forename: Eric M
authors.initials: EM
authors.lastname: Phillips
authors.forename: Matthias
authors.initials: M
authors.lastname: Riedrich
authors.forename: Karl A
authors.initials: KA
authors.lastname: Scheidt
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000438:Alcohols; D006571:Heterocyclic Compounds; C030011:carbene; D008697:Methane
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