Conjugate reduction of alpha,beta-unsaturated carbonyl compounds catalyzed by a copper carbene complex.
[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.
Jurkauskas
Valdas
V
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Sadighi
Joseph P
JP
Buchwald
Stephen L
SL
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006838:Hydrocarbons; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry*
D006838:Hydrocarbons; C030011:carbene; D003300:Copper; D008697:Methane