Lewis Acid-Catalyzed Nucleophilic Substitutions of Benzylic Alcohols with Sulfamides

Nucleophilic substitutions of benzylic alcohols with sulfamides were achieved using an FeCl3 Lewis acid catalyst in MeNO2. It was necessary to adjust the reaction conditions to obtain efficient yields depending on the stability of the carbocation intermediates. The reaction could easily be performed, and it was revealed that a variety of diarylmethanols and benzylic alcohols were applicable to the reaction, irrespective of the type and position of the substituents. The sulfamide moieties were easily deprotected and converted into amine groups.

Automated summary

The nucleophilic substitutions of benzylic alcohols with sulfamides were successfully achieved using an FeCl3 Lewis acid catalyst in MeNO2. The reaction conditions needed to be adjusted depending on the stability of the carbocation intermediates to obtain efficient yields. Various diarylmethanols and benzylic alcohols were applicable to the reaction, and the sulfamide moieties could be easily deprotected and converted into amine groups.