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Cu_Zn_Organometallics

its all about organometallic chemistry of zinc and copper metal

Reaction of

Reaction of Organocuprates • Conjugate additions of organocopper reagents with large steric requirements and/or when there is steric hindrance at the reaction center of the enone may be difficult. • Addition of Me 3 SiCl accelerates the conjugate additions of copper reagents to such enones, probably by activating the carbonyl group. • For example, 3-methylcyclohexenone is essentially inert to n- Bu 2 CuLi at –70 °C in THF. • However, in the presence of Me 3 SiCl the enolate initially formed is trapped to give the β-disubstituted silyl enol ether in 99% yield. Hydrolysis of the silyl enol ether regenerates the carbonyl group.

Reaction of Organocuprates • Reactions of β,β-disubstituted enones with organocuprates are often not very successful because of steric of the C=C. • In these cases, use of R 2 CuLi–BF 3 •OEt 2 often obviates the problem. Possibly, Lewis acid BF 3 further polarizes and activates the ketone by coordination. • Grignard reagents in the presence of CuX or a mixture of MnCl 2 and CuI undergo 1,4-addition to hindered enones.

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