Chemistry of Organolanthanoids. Lanthanoid-Mediated C-C Bond Formation and Cleavage and C-C Double Bond Reduction

Article abstract of DOI:10.1021/jo00392a006

Reactions of the organolanthanoid ?-complexes RLnI with α,β-unsaturated carbonyl compounds and allylic alcohols under various conditions are described.An equivalent of RYbI reacts with α,β-unsaturated carbonyl compounds to give 1,2-addition products 1 regioselectively.On the other hand, the reaction of an excess of RYbI with chalcone gives C-C bond cleavage products 2 and 4 and deoxygenation product 3 instead of 1.In the reactions of PhYbI with benzalacetone or cinnamyl alcohol, compounds 5, derived from addition of RYbI to the C-C double bonds of the substrates, are obtained as main products.An excess of PhEuI reacts with α,β-unsaturated carbonyl compounds to give 2-4.C-C double bonds conjugated with phenyl group are hydrogenated by PhYbI/MeOH.Reduction of trans-stilbene with Yb/MeOD gives the deuteriated product 6a.