Metal-free visible-light-induced multi-component reactions of α-diazoesters leading to S-alkyl dithiocarbamates

Abstract

A metal-free and visible-light-promoted strategy has been developed for the synthesis of S-alkyl dithiocarbamates through multicomponent reactions of α-diazoesters, amines and CS2.

Visible light-mediated photolysis of organic molecules: the case study of diazo compounds

“…74 Several multicomponent reactions involving the use of cyclic ethers as solvent and a variety of nucleophiles have been reported to afford the corresponding more complex formal O-H insertion products, which are also presumably derived from the involvement of a key oxygen ylide intermediate. 61,62,64,[75][76][77][78][79][80][81][82][83][84] C-C insertion reactions could be achieved with 1,3-diketones 85,86 (with a rare successful example of enantioselective catalysis being demonstrated by Hui and co-authors employing a chiral phosphoric acid catalyst 86 ), and enaminones. 87 Condensation-type products have been also obtained starting from azides to afford imines, 34 and starting from isonitriles to afford ketenimine derivatives.…”

A Decade of Advances of CS2/Amines in Three-Component Reactions

“…Wei, Zhao, He, and co-workers 21b have developed visible-light-induced reactions of α-diazo esters 18.5 with secondary amines and CS 2 using dioxane as the solvent and DBU as a base to give S -carboxymethyl dithiocarbamates (Scheme 18 ). Using THF as the solvent gave S -4-(carboxymethoxy)butyl dithiocarbamates 18.6 by a novel four-component reaction.…”

Fe-mediated oxidative cascade [1 + 2 + 3]-cyclization/esterification reaction: synthesis of 4-alkylated 1,4-dihydropyridines

“…14 Meanwhile, an effective approach for the tandem cleavage of C(sp 3 )–H and C(sp 3 )–O bonds of cyclic ethers to the bifunctionalized chain molecules through the 1,1-bifunctionalization reaction has been developed. 15 Although great progress has been made in ring-opening bifunctionalization reactions, the transformation of cyclic ethers involving a further cyclization reaction for the synthesis of highly functionalized cyclic compounds through MCRs is less studied. 16 Particularly, selectively functionalizing the oxygen of cyclic ethers to obtain high-value-added heterocycles has never been demonstrated in a one-pot manner, which is an important synthetic challenge (Scheme 1c).…”