Copper-catalyzed cross-coupling reaction of epoxides with allyl boron ester

Abstract

Herein, a copper-catalyzed ring-opening cross-coupling reaction of epoxides with allylboronates for the synthesis of γ-alkenyl alcohols is reported. This protocol demonstrates broad functional group compatibility, facilitating the production of secondary and tertiary alcohols from both monosubstituted and 1,1-disubstituted epoxides. Mechanistic studies indicate that the reaction proceeds via an iodide-mediated ring-opening pathway. Additionally, gram-scale synthesis and subsequent derivatizations confirm the practical utility of this method for generating intermediates in pharmaceuticals and natural products.