Calcium-catalyzed regioselective dehydrative cross-coupling of propargylic alcohols with 1,3-dicarbonyl compounds?

Green Chemistry Pub Date: 2019-09-03 DOI: 10.1039/C9GC02635E

Abstract

A novel calcium-catalyzed in situ dehydrative cross-coupling reaction of propargylic alcohols with 1,3-dicarbonyl compounds was developed. This catalytic system can suppress the competitive Meyer–Schuster rearrangement, control regioselectivity, and enable the desired process to occur under solvent-free conditions at room temperature with water as the only byproduct. A variety of vicinal tertiary and all-carbon quaternary centers can be obtained in high yields with broad functional group tolerance.

Graphical abstract: Calcium-catalyzed regioselective dehydrative cross-coupling of propargylic alcohols with 1,3-dicarbonyl compounds
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