An Efficient Copper-Catalyzed C(sp2)–S Formation Starting from Aryl Iodides and Tetramethylthiuram Monosulfide (TMTM)

Abstract

A new, efficient copper-catalyzed C(sp2)–S formation of phenyl dithiocarbamates starting from aryl iodides and tetramethylthiuram monosulfide (TMTM) was developed. The target compounds, phenyl dithiocarbamates with active sites, were synthesized smoothly in good to excellent yields. The easy performance, high yields, decent functional group compatibility, and cost-effective substrates make the protocol practical and attractive in C–S bond formation.

Copper-Promoted Hiyama Cross-Coupling of Arylsilanes With Thiuram Reagents: A Facile Synthesis of Aryl Dithiocarbamates

“…With regard to the reaction pathway between 1a and 5 (TMTM), a plausible ionic-type reaction mechanism was tentatively proposed according to the obtained results as well as the reported literatures ( Dong et al, 2017 ; Luo et al, 2020 ; Wu et al, 2020 ) and described in Scheme 5 . Analogously, the initial coordination of bipyridine with copper salts to produce the copper complex F. Concurrently, the intermediate G is generated by the C-Si cleavage manner, which activated by fluoride ion ( Sugiyama et al, 2008 ).…”

“…To further evaluate the applicability of this reaction, the reactivity of trimethoxy (phenyl)silane (1a) was investigated using tetramethylthiuram monosulfide (TMTM, 5) as the coupling partner ( Wu et al, 2020 ). As expected, the cross-coupling reaction occurred smoothly, and the phenyl dimethylcarbamodithioate 3a was formed in 46% yield ( Scheme 2 ).…”