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

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 acid 3 and sulfoxides 4 , 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 thiocarbamates 9 . Aromatic systems with sulfur-containing substituents have also been prepared by nucleophilic addition to quinones 10,11 or their mono 12 or diketals 13 .