A Radical FLP Approach to C–C Coupling

Abstract

In the February issue of Cell Reports Physical Science, Melen and co-workers report the reactivity of diaryl-substituted esters with R3P/B(C6F5)3 frustrated Lewis pairs (FLPs). Although ester C–O activation occurs for all FLP systems, the use of Mes3P induces single-electron transfer to generate a [Mes3P]⋅+/[C(H)Ar2]⋅ radical ion pair. In the presence of olefins, this reactivity is harnessed in an sp2-sp3 C–C heterocoupling reaction to generate α,β-substituted olefins.