Transition-Metal-Free Coupling Reaction of Dithiocarbamates with Indoles: C–S Bond Formation

Abstract

A one-pot three-component route for the direct introduction of dithiocarbamates into indoles using a C-H sulfenylation strategy mediated by molecular iodine is disclosed. Various indole derivatives including 1-methylindole, 2-methylindole, 3-methylindole, and 5-substituted indoles were applied successfully in this protocol to afford diverse indole-dithiocarbamates containing the dithiocarbamate group on the position two or three in good to high yields. The reactions do not require transition metals or disulfiram but use an environmentally benign solvent and simple commercially available starting materials.

Recent Advances in Iodine‐Promoted C−S/N−S Bonds Formation

“…[92] Ta king these factors into consideration, on the basis of Ta ng's report in 2016, [69] Beier and co-workers discloseda ni odine-mediated one-pot three-componentr eaction for the synthesis of indoledithiocarbamates 113 from the secondary amines, CS 2 ,a nd indoles (Scheme 37). [93] This metal-free method proceeded in an environmentallyb enign solventa nd allowed for an efficient introduction of the dithiocarbamate group by CÀHs ulfenylation of indoles at C2 or C3 position, which was different from the above reports that only 3-sulfenylindoles derivatives could be obtained. In the mechanism studies, the authorsp roposed the reactive intermediate II was formed involved two pathways, which reacted with indoles to generate the terminal products.…”

Recent Advances in Multicomponent Reactions with Organic and Inorganic Sulfur Compounds

“…The three‐component coupling reaction starting from indole, secondary amines and carbon disulfide under environmentally benign solvent conditions led to indole‐dithiocarbamates 77 in moderate yields (Scheme 19). [60] Its main advantage was used an environmentally benign solvent and simple commercially available starting materials.…”

C‐S cross‐coupling reaction using novel and green synthesized CuO nanoparticles assisted by Euphorbia maculata extract

“…Cross‐coupling reactions have been used as powerful and useful synthetic tools in novel synthetic chemistry . The formation of C − S bonds is momentous in synthetic organic chemistry for the structure of different synthetics, a large number of drugs for diseases such as diabetes, cancer, Alzheimer's, Parkinson's, or inflammatory HIV diseases, and natural biologically active compounds (Figure ) …”

“…[5,[41][42][43] The formation of C − S bonds is momentous in synthetic organic chemistry for the structure of different synthetics, a large number of drugs for diseases such as diabetes, cancer, Alzheimer's, Parkinson's, or inflammatory HIV diseases, and natural biologically active compounds ( Figure 1). [44][45][46] Recently, aryl sulfides and their derivatives have drawn much attention in molecular precursors for the development of this materials because of their biological, pharmaceutical properties. [47][48][49][50][51] Therefore, transitionmetal-catalyzed C-S bond formation has been the subject of many studies in the last few decades.…”