An Improved Protocol for the Synthesis of Carbonyl Sulfoxonium Ylides

Abstract

An improved protocol for the synthesis of carbonyl sulfoxonium ylides from the reaction between trimethylsulfoxonium iodide and reactive carboxylic acid derivatives is described. In a one-pot, two-step sequence, these sulfoxonium ylides could be obtained in up to 81% yield with shorter reaction times and lesser equivalent numbers of the reactants when compared to the previous methods. These improvements make the method less expensive and ideal for larger scale preparations as well, not necessitating excess of the trialkylsulfoxonium salt starting material. An easier workup procedure, avoiding solvent extraction, is also discussed and facilitates product isolation.

Key words

sulfur - sulfoxonium ylides - carbonyl - acylation - ketones

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