Palladium-Catalyzed Alkynylation of Enones with Alkynylsilanes via C-C Bond Activation

We report herein the synthesis of 1,3-enynes via palladium-catalyzed cross-coupling between enone derivatives and alkynylsilanes. The employment of an appropriate pyridine-oxazoline ligand is the key to the C-C cleavage and the high E/Z stereoselectivity. This protocol features broad substrate scope and wide functional-group tolerance, affording the desired products in moderate-to-good yields. Late-stage diversification of natural product beta-ionone further demonstrated the synthetic utility of this protocol.

Automated summary

In this study, we report the synthesis of 1,3-enynes through palladium-catalyzed cross-coupling between enone derivatives and alkynylsilanes. The use of an appropriate pyridine-oxazoline ligand is crucial for achieving C-C cleavage and high E/Z stereoselectivity. This method demonstrates broad substrate scope, wide functional-group tolerance, and moderate-to-good yields. Furthermore, the late-stage diversification of natural product beta-ionone showcases the synthetic utility of this protocol.