Metallation - Sulfidation: A Convenient Method for the Synthesis of Aryl Alkyl Sulfides and of Unsymmetrical Diaryl Sulfides

Abstract

A number of procedures have been employed for the synthesis of sulfur-substituted aromatics; e.g., electrophilic substitution with sulfur-containing electrophiles such as sulfenyl halides^1,2, chlorosulfonic acid³ and sulfoxides⁴, nucleophilic substitution of aryl halides with metal mercaptides^5,6, replacement reactions involving diazonium intermediates^7,8, and conversion of phenols to thiophenols via thermal rearrangement of thiocarbamates⁹. Aromatic systems with sulfur-containing substituents have also been prepared by nucleophilic addition to quinones^10,11 or their mono¹² or diketals¹³.