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DOI: 10.1055/sos-SD-027-00002

Aggarwal, V.; Richardson, J.Science of Synthesis, (20042763.

The phase-transfer-catalyzed transfer of anionic reactants, such as basic hydroxide anions, from an aqueous to an organic phase by quaternary ammonium salts is a commonly used procedure for the deprotonation of sulfonium salts. Using aqueous sodium hydroxide and dichloromethane in the presence of a quaternary ammonium salt, typically tetrabutylammonium chloride or benzyltriethylammonium chloride, a range of sulfonium ylides can be prepared, including those that are unsubstituted,[‌131‌,‌200‌] those bearing aryl groups,[‌201‌] and carbonyl stabilizing groups.[‌202‌]