Regiocontrol in palladium-catalysed allylic alkylation by addition of lithium iodide

Abstract

Regioselectivity in the palladium-catalysed allylic alkylation of 1-arylprop-2-enyl acetates [ArCH(OAc)CH[double bond, length half m-dash]CH₂] or (E)-3-phenylprop-2-enyl acetate (PhCH[double bond, length half m-dash]CHCH₂OAc) with sodium enolates of soft carbon nucleophiles is controlled by addition of a catalytic amount of lithium iodide to give lienar products [(E)-ArCH[double bond, length half m-dash]CHCH₂Nu] exclusively; their branch isomers [ArCH(Nu)CH[double bond, length half m-dash]CH₂] were not detected.

References

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