Visible-Light-Enabled Stereodivergent Synthesis of E- and Z-Configured 1,4-Dienes by Photoredox/Nickel Dual Catalysis

Abstract

A stereodivergent reductive coupling reaction between allylic carbonates and vinyl triflates to furnish both E- and Z-configured 1,4-dienes has been achieved by visible-light-induced photoredox/nickel dual catalysis. The mild reaction conditions allow good compatibility of both vinyl triflates and allylic carbonates. Notably, the stereoselectivity of this synergistic cross-electrophile coupling can be tuned by an appropriate photocatalyst with a suitable triplet-state energy, providing a practical and stereodivergent means to alkene synthesis. Preliminary mechanistic studies shed some light on the coupling step as well as the control of the stereoselectivity step.

Keywords: cross-coupling; nickel; photochemistry; reaction mechanisms; stereochemistry.