Patent ID: 7173139

Claim:
A method for carrying out a 1,4-addition reaction between an aromatic nucleophile and an Î±,Î²-unsaturated aldehyde, comprising contacting an Î±,Î²-unsaturated aldehyde with an aromatic nucleophile having the structure of formula (IV) in the presence of a catalyst having the structure of formula (IIA) or (IIB) or an acid addition salt thereof, wherein: R 1 is selected from C 1 â€“C 12 hydrocarbyl, substituted C 1 â€“C 12 hydrocarbyl, heteroatom-containing C 1 â€“C 12 hydrocarbyl, and substituted heteroatom-containing C 1 â€“C 12 hydrocarbyl; R 2 has the structure â€”(L) m â€”CR 6 R 7 R 8 wherein m is zero or 1, L is C 1 â€“C 6 alkylene, and R 6 , R 7 and R 8 are C 1 â€“C 12 hydrocarbyl; R 3 and R 4 are independently selected from hydrogen, halo, hydroxyl, C 1 â€“C 12 hydrocarbyl, substituted C 1 â€“C 12 hydrocarbyl, heteroatom-containing C 1 â€“C 12 hydrocarbyl, and substituted heteroatom-containing C 1 â€“C 12 hydrocarbyl; and R 5 is a cyclic group optionally substituted with 1 to 4 non-hydrogen substituents and containing zero to 3 heteroatoms, Q is an electron-donating group; and R 12 and R 13 are independently selected from hydrogen, C 1 â€“C 30 hydrocarbyl, heteroatom-containing C 1 â€“C 30 hydrocarbyl, substituted C 1 â€“C 30 hydrocarbyl, substituted heteroatom-containing C 1 â€“C 30 hydrocarbyl, and functional groups, or R 12 and R 13 , or R 12 and an atom within Q, taken together, form a cyclic structure selected from five-membered rings, six-membered rings, and fused five-membered and/or six-membered rings, wherein the cyclic structure is aromatic or alicyclic, substituted with zero to 4 non-hydrogen substituents and contains up to 3 heteroatoms per ring.