title: Acrylamide in the Baylis-Hillman reaction: expanded reaction scope and the unexpected superiority of DABCO over more basic tertiary amine catalysts.
abstract: DMAP, DBU, and quinuclidine efficiently promote novel hydroalkoxylation reactions of acrylamide in primary alcohol solvents. DABCO is a comparatively poor hydroalkoxylation promoter and can effect clean, selective Baylis-Hillman reactions between acrylamide and aldehydes in alcoholic/aqueous media in which more basic nucleophilic catalysts promote hydroalkoxylation preferentially. Optimization of the reaction conditions has allowed acrylamide to be reacted with a range of aromatic aldehydes in moderate to excellent yields, including the first examples involving deactivated, electron-rich substrates such as p-tolualdehyde and o-anisaldehyde.
authors.affiliation: Department of Chemistry, Trinity College Dublin, Dublin 2, Ireland.
authors.forename: Cornelia
authors.initials: C
authors.lastname: Faltin
authors.forename: Eimear M
authors.initials: EM
authors.lastname: Fleming
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Connon