Facile Synthesis of Thiols and Sulfides

Abstract

Sulfurated sodium borohydride reacts with benzylic halides to give high yields of α-toluenethiol or benzylic polysulfldes depending upon the experimental conditions and the mode of hydrolysis.Aliphatic halides and dibenzylic halides react in the same manner as benzylic halides for a given experimental condition whereas benzylic halides substituted with other groups can be totally or partially reduced depending on the stability of the substituent towards NaBH2S3.Halogens directly attached on the aromatic ring do not react with NaBH2S3.

Facile thiolation of hydroxyl functional polymers

“…This is largely due to the fact that conventional thiolation strategies require harsh conditions, e.g. bases, 26,27 halides 28 or polycondensation, 29 making them incompatible with more delicate structures such as esters. These protocols also result in inherent dispersity, making them unsuitable for the preparation of precision polymers such as dendrimers.…”