Synthesis of Diaryl Sulfides by Using Tetramethylthiuram Monosulfide (TMTM) as Organosulfur Source: A Practical C(sp²)−S Bond Construction

Abstract

A protocol for synthesizing symmetrical thioethers by using a cheap organosulfur reagent (tetramethylthiuram monosulfide: TMTM) was developed. Both iodobenzenes and phenylboronic acids react well with TMTM, giving the target products with good to excellent yields. This method features simple performance, wide functional group tolerance, and good to excellent yields, showing a potential application value for the synthesis of drug molecules.

Access to Sulfur-Containing Bisheterocycles through Base-Promoted Consecutive Tandem Cyclization/Sulfenylation with Elemental Sulfur

“…However, unpleasant odor, difficulty in preparation, and instability under air atmosphere limit their applications. Recently, some new synthesis strategies involving the use of carbon disulfide (CS 2 ), tetramethylthiuram disulfide (TMTD), and elemental S 8 were reported. − In 2019, Yang and co-workers reported that the copper-catalyzed domino reactions involving CS 2 could provide a series of C-3 sulfenylated imidazo­[1,2- a ]­pyridine derivatives (Scheme a) . Subsequently, Dong’s group developed an iodine mediated, TMTD-enabled method for constructing benzoazole-substituted thioenamines (Scheme b) .…”

“…Recently, some new synthesis strategies involving the use of carbon disulfide (CS 2 ), tetramethylthiuram disulfide (TMTD), and elemental S 8 were reported. − In 2019, Yang and co-workers reported that the copper-catalyzed domino reactions involving CS 2 could provide a series of C-3 sulfenylated imidazo­[1,2- a ]­pyridine derivatives (Scheme a) . Subsequently, Dong’s group developed an iodine mediated, TMTD-enabled method for constructing benzoazole-substituted thioenamines (Scheme b) . In 2021, Chaubey and co-workers described HFIP promoted thio­(hetero)­arylation of imidazoheterocycles with chloroheteroarenes (Scheme c) .…”