Tunable 1,3-Lithium Shift of Propargylic/Allenylic Lithiums Formed by ­Conjugate Addition of 4-Aryl-3-butyn-1-enes with Organolithiums and the Subsequent Transmetalation/Pd(0)-Catalyzed Coupling Reaction with Aryl Halides

Abstract

A protocol was established to control the 1,3-lithium shift in propargylic/allenylic species formed by the conjugate addition of 4-aryl-3-butyn-1-enes with organolithiums. Subsequent transmetalation and Pd(0)-catalyzed cross-coupling with aryl halides afforded 1,1-diarylallenes and 1,3-diarylallenes, respectively, the structural diversities of which are determined by the easily availability of both 4-aryl-3-butyn-1-enes and the organolithium reagents.

Key words

conjugated enynes - organolithiums - conjugate addition - Negishi coupling - allenes

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1

There are 22672 allene reactions summarized in Beilstein data.