Transition-metal free reactions of boronic acids: cascade addition– ring-opening of furans towards functionalized c-ketoaldehydes

Abstract

We describe the first ring-opening of furfuryl alcohols with boronic acids to afford functionalized c-ketoaldehydes. The transformation builds a new C–C bond at the original C-4 of the starting furan, and tolerates ring-substitution at C-3 and C-4 positions. The reaction takes place under metal-free conditions by promotion with tartaric acid.