A Simple, Fast and Chemoselective Method for the Preparation of Arylthiols

摘要

An efficient and convenient method for the synthesis of arylthiols by reaction of sulfonyl chlorides with triphenylphosphine in toluene is reported. General strategies for the synthesis of arylthiols include transition-metal-mediated electrophilic or nucleophilic substitution, followed by dealkylation to the arylthiol. Another method is thiolation of haloaryls using metal sul-fides such as sodium hydrogen sulfide or disodium disul-fide, however, this method is only useful when the aryl ring contains an electron-withdrawing group, whereas al-kanethiolate salts can be used for thiolation of non-activated arenes. Nucleophilic substitution of aryl iodides with thiourea in the presence of a transition-metal catalyst gives S-arylisothiouronium salts which, after hydrolysis, afford the thiol. For the synthesis of alkoxyarylthiols or aminoarylthiols (Herz reaction), disulfur dichloride has been used with various metal salts. Mono-halogen substituted arylthiols have been prepared using poly sulfide. Catalytic reaction of phenol with hydrogen sulfide in the gas phase has also been used. Arylthiols have also been prepared from phenol by a Newman-Kwart rearrangement, and anilines through Leukart thiophenol synthesis.