Cu(I)-catalyzed cross-coupling of conjugated ene-yne-ketones and terminal alkynes: synthesis of furan-substituted allenes

Org Lett. 2014 Aug 15;16(16):4082-5. doi: 10.1021/ol501747f. Epub 2014 Jul 30.

Abstract

A new method for the synthesis of furan-substituted allenes via Cu(I)-catalyzed coupling of conjugated ene-yne-ketones with terminal alkynes has been developed. A wide range of functional groups are tolerated, and the products are obtained in good to excellent yields under mild conditions. A copper carbene migratory insertion is proposed as the key step in this transformation with conjugated ene-yne-ketones as carbene precursors.