Base-catalyzed stereoselective thiosulfonylation of ynones for the facile synthesis of thio-functionalized vinyl sulfones

Abstract

The first catalytic vicinal thiosulfonylation and trifluoromethylthiosulfonylation of ynones have been developed. Under the catalysis of 1-20 mol% Cs2CO3, various ynones underwent Michael addition/nucleophilic substitution tandem reaction with different thiosulfonates...

Recent advances in the dichalcogenation reactions of unsaturated compounds via double functionalization

“…Very recently, He and coworkers reported the synthesis of a series of aryl/alkylthiolated vinyl sulfones 68c via Cs 2 CO 3 -catalyzed highly trans -selective thiosulfonylation of ynones 68a with S -alkyl/aryl-substituted thiosulfonates 68b (Scheme 68). 95 By using K 3 PO 4 as the base, ynones also reacted with various S -trifluoromethyl thiosulfonates to afford the corresponding trifluoromethylthiolated vinyl sulfones 68c in good to high yields. The base was found to be critical for the reaction since no product was generated in its absence.…”

“…Scheme95 Wang's electrooxidative radical cyclization of 2-alkynylthioanisoles with sodium sulfinates.…”

Trace water in a BF3·OEt2 system: a facile access to sulfinyl alkenylsulfones from alkynes and sodium sulfinates

“…5 Owing to the interest in its synthesis, 6 there are numerous synthetic methods for vinyl sulfone synthesis. 7 Usually, the difunctionalization of alkynes 8 can provide an efficient and direct way via the concomitant introduction of two different functional groups 9 (Scheme 1a). For instance, Tang's group 10 reported a direct disulfonylation reaction of terminal alkynes and sodium sulfinates with a Cu( i ) catalyst (Scheme 1b).…”

Iodine-Promoted Disproportionate Coupling Reaction of Arylsulfonyl Hydrazides: A Simple and Green Access to Thiosulfonates

“…3 Among them, thiosulfonates contain sulfonyl groups and thioether bond. These two functional groups make them become remarkable synthons in organic synthesis, especially in sulfonylation reaction [4][5][6] and thioetherification reaction. [7][8][9] Additionally, thiosulfonates possess various potential biological activities, such as antiviral 10 and anticancer.…”