Aryne Three-Component Coupling Involving CS₂ for the Synthesis of S-Aryl Dithiocarbamates

Abstract

A facile synthesis of biologically important S-aryl dithiocarbamates has been demonstrated by the aryne three-component coupling involving CS2 and aliphatic amines. This transition-metal-free and mild reaction is scalable and operates with good functional group compatibility. Preliminary mechanistic experiments, including density functional theory studies, are also provided. Moreover, with 3-triflyloxybenzynes, a unique four-component coupling incorporating tetrahydrofuran was observed.

Recent Advances in Construction of C(sp2)–O Bonds via Aryne Participated Multicomponent Coupling Reactions

“…In 2021, Biju and co-workers also accomplished a similar four-component reaction involving 3-(triflyloxy)benzynes, THF, CS 2 , and aliphatic amines. 11b In the same report, they also demonstrated the three-component synthesis of S -aryl dithiocarbamates and provided deep insights into the mechanistic aspects by both experimental and DFT calculation studies.…”

Poly(ethylene glycol) Dimethyl Ethers (PEGDME): Efficient and Recyclable Solvents for Aryne-Involved Reactions

“…The desired product 23 was formed in 92% yield from piperidine (21) and carbon disulfide (22) (Scheme 3d). 19 A three-component reaction of 4-fluorothiophenol ( 24) and 4-chlorobenzaldehyde (25) with aryne 2 in PEGDME resulted in compound 26 (68% yield) (Scheme 3e). 20 In addition, a one-pot multi-component reaction of phenyl acetylene (27), diisopropylcarbodiimide (28) and two equivalents of aryne 2 in PEGDME afforded 2-aminophenyl alkynyl imine 29 in 86% yield (Scheme 3f).…”

Synthesis of Tritylones via Cascade Reaction of Arynes with 5-Ethoxyoxazoles

“…In these reactions, different atoms of the oxazole are incorporated into the product, while maintaining their bond connectivity (Scheme a). We envisioned a route toward the substituted phenanthrone motif via their reaction with arynes, which are adept at providing access to new molecular architectures . In our proposed construct (Scheme c), two structural components of 5-ethoxyoxazole would feature in the product, but at remote sites.…”