Simple and efficient nickel-catalyzed cross-coupling reaction of alkenylalanes with alkynyl halides for synthesis of conjugated enynes

A NiCl2(PPh3)(2)/XantPhos catalyzed synthesis of conjugated enynes by the cross-coupling of terminal alkynyl halides with alkenylaluminum reagents at room temperature in DME solvent was developed under mild reaction conditions. The aryls bearing electron-donating or electron-withdrawing groups in alkynylhalides give the corresponding cross-coupling products conjugated enynes in good to excellent isolated yields up to 97%. This process was simple and easily performed, which provides an efficient method for the synthesis of conjugated enynes derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed. (C) 2021 Elsevier Ltd. All rights reserved.

Automated summary

A catalytic synthesis of conjugated enynes was developed using NiCl2(PPh3)(2)/XantPhos catalysts in DME solvent, by the cross-coupling of terminal alkynyl halides with alkenylaluminum reagents. This method is simple and efficient, providing high yields of conjugated enynes and is suitable for a variety of aryl alkynyl halides.