Rapid and Controlled Assembly of Polysubstituted Furans and Their Oligoaryls from Alkynes and Aldehydes Facilitated by Sequential Deprotonation.

A new sequential deprotonation strategy of dimethyl sulfoxide (DMSO) and propargyl alcohol in the presence of a base was developed for the generation of the α-hydroxyl carbanion, which enables rapid and controllable access to a wide range of valuable highly functionalized furans in one pot from alkynes and aldehydes under transition-metal- and additive-free conditions. Preliminary mechanistic studies revealed the crucial role of the base and DMSO. More importantly, deuterium labeling experiments confirmed the formation of the α-hydroxyl carbanion.