Rapid and Controlled Assembly of Polysubstituted Furans and Their Oligoaryls from Alkynes and Aldehydes Facilitated by Sequential Deprotonation
Yiqing Wang1,2, Yue Hu2,3, Liqun Jin1
1College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
Abstract:
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.
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