Synthesis of 3-(Arylthio)propionic Acids from Nonactivated Aryl Iodides and their Use as Odorless Aryl Mercaptan Surrogates

Abstract

Abstract The reaction of aryl iodides, 3-mercaptopropionic acid, and Cu2O in refluxing pyridine resulted in the formation of 3-(arylthio)propionic acids in good to excellent yield. The latter 3-(arylthio)propionic acids — as novel aryl mercaptan equivalents — gave aryl mercaptans or diaryl disulfides, respectively, on reductive (Na2S) or oxidative (I2) cleavage in alkaline media. The symmetrical disulfides can also be prepared by oxidizing their precursor mercaptans with phenyltrimethyl­ammonium­tribromide in pyridine at ambient temperature.

Keywords

• 3-mercaptopropionic acid
• sulfur-transfer reagent
• 3-(aryl­thio)propionic acid
• reverse michael reaction
• copper(i) oxide