One-Pot Morita-Baylis-Hillman/Allylic Substitution in Deep Eutectic Solvents: Access to γ-Hydroxy Derivatives via Sequential CC and CX (X = P, N, S, B, Si) Bond Formation.

ABSTRACT: A sustainable one-pot sequential CC/CX (X = P, N, S, B, Si) bond-forming strategy for synthesizing functionalized γ-hydroxy derivatives using ChCl/Gly (1:2) (ChCl = choline chloride and Gly = glycerol) deep eutectic solvent (DES) is reported. The methodology combines 1) an atom-economical Morita-Baylis-Hillman reaction for CC bond formation and 2) subsequent nucleophilic functionalization to afford diverse γ-hydroxy derivatives in good yields under mild, air/moisture-tolerant conditions. The DES system enables straightforward product isolation via water-induced precipitation, eliminating, in most of the cases, chromatographic purification. Notably, sulfinic acid reactivity displays striking stoichiometric control: 2 equiv. RSO₂H yields γ-hydroxy sulfones, while 1 equiv. selec

SUBMITTER: Ramos-Martin M 

PROVIDER: S-EPMC12767280 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature