title: Conjugate reduction of alpha,beta-unsaturated carbonyl compounds catalyzed by a copper carbene complex.
abstract: [reaction: see text] An N-heterocyclic carbene copper chloride (NHC-CuCl) complex (2) has been prepared and used to catalyze the conjugate reduction of alpha,beta-unsaturated carbonyl compounds. The combination of catalytic amounts of 2 and NaOt-Bu with poly(methylhydrosiloxane) (PMHS) as the stoichiometric reductant generates an active catalyst for the 1,4-reduction of tri- and tetrasubstituted alpha,beta-unsaturated esters and cyclic enones. The active catalytic species can also be generated in situ from 1,3-bis(2,6-di-isopropylphenyl)-imidazolium chloride (1) CuCl(2).2H(2)O in the presence of NaOt-Bu and PMHS.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
authors.forename: Valdas
authors.initials: V
authors.lastname: Jurkauskas
authors.forename: Joseph P
authors.initials: JP
authors.lastname: Sadighi
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Buchwald
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006838:Hydrocarbons; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D006838:Hydrocarbons; C030011:carbene; D003300:Copper; D008697:Methane