Catalyst-free synthesis of α,α-disubstituted carboxylic acid derivatives under ambient conditions via a Wolff rearrangement reaction

Herein, a hexafluoroisopropanol (HFIP)-promoted Wolff rearrangement reaction was developed, delivering various alpha,alpha-disubstituted carboxylic acid derivatives in good to excellent yields. In this reaction, alpha-diazoketone could be activated using HFIP under mild conditions via hydrogen bonding between hydroxyl and carbonyl groups.

Automated summary

A HFIP-promoted Wolff rearrangement reaction has been developed for the synthesis of various alpha,alpha-disubstituted carboxylic acid derivatives in good to excellent yields. The activation of alpha-diazoketone using HFIP under mild conditions is achieved via hydrogen bonding between the hydroxyl and carbonyl groups.