Three-component approach to modular synthesis of tetra-substituted furans and pyrroles

Abstract

The exploration of novel chemical reactivities of readily available feedstocks has always been a hot topic in the synthetic community. We herein report a three-component one-pot reaction with TMSCF₂Br, p-QMs and 1,3-dicarbonyl compounds and analogues, providing a modular protocol for the construction of densely functionalized tetrasubstituted furans and pyrroles. While TMSCF₂Br has been widely used as a difluorocarbene or trimethylsilyldifluoromethyl radical precursor, it herein acts as a surrogate of “naked” carbon. Control experiments indicate that repeated substitution/elimination processes are involved. This reaction features high step-economy, mild conditions and excellent chemoselectivity. The phenolic hydroxyl groups of products offer a platform for the late-stage modification of furans and pyrroles, which could enrich the structural diversity of the products rapidly.