Sulfonylation Of Alkenes Research Articles

Photoredox‐Catalyzed Functionalization of Alkenes with Thiourea Dioxide: Construction of Alkyl Sulfones or Sulfonamides

Summary of main observation and conclusionSulfonylation of alkenes through photoredox‐catalyzed functionalization of alkenes with thiourea dioxide under visible‐light irradiation is achieved. The reaction of alkenes, thiourea dioxide and electrophiles provides a green and efficient access to alkyl sulfones and sulfonamides. A broad reaction scope is presented with good functional group compatibility and excellent regioselectivity. A plausible mechanism involving a radical addition process with sulfur dioxide radical anion (SO2‐) derived from the oxidation of sulfur dioxide anion (SO22–) is proposed, which is supported by fluorescence quenching experiments.

The continuous-flow electrosynthesis of 4-(sulfonylmethyl)isoquinoline-1,3(2H,4H)-diones from N-alkyl-N-methacryloyl benzamides under metal-free and oxidant-free conditions

An efficient and green electrochemical continuous flow approach has been developed for the synthesis of 4-(sulfonylmethyl)isoquinoline-1,3(2H,4H)-diones through sulfonylation of alkenes under metal-free and oxidant-free conditions.

Visible-Light Photocatalytic Remote Thiolation of Aldehydes Triggered by Sulfonylation of Alkenes With Thiosulfonates

Visible-Light Photocatalytic Remote Thiolation of Aldehydes Triggered by Sulfonylation of Alkenes With Thiosulfonates

Recent advances in the sulfonylation of alkenes with the insertion of sulfur dioxide via radical reactions.

Recent advances in the sulfonylation of alkenes via the insertion of sulfur dioxide are summarized. The sulfur dioxide surrogate of DABCO·(SO2)2 or inorganic sulfites is used in the transformation through a radical process. Two strategies for the sulfonylation of alkenes with the insertion of sulfur dioxide have been developed. In most cases, the vicinal difunctionalization of alkenes is initiated by the arylsulfonyl radical generated in situ. Although the sulfonylation of alkenes with the insertion of sulfur dioxide is efficient, the asymmetric versions are still challenging and less to be explored. It is expected that the asymmetric vicinal difunctionalization of alkenes with the insertion of sulfur dioxide will be developed rapidly in the near future.

Visible-Light-Induced Chemoselective Synthesis of α-Chloro and Vinyl Sulfones by Sulfonylation of Alkenes

Direct sulfonylation between alkenes and sulfonyl chloride was achieved at room temperature by a visible-light-induced photo­redox process. This method allows the chemoselective synthesis of α-chloro and vinyl sulfone derivatives with moderate to high yields. The selectivity of the reaction was fully controlled by the electronic properties of the alkenes.

Copper‐Catalyzed Sulfonylation of Alkenes and Amines by Using Thiosulfonates as a Sulfonylating Agent

Synthetically and pharmaceutically useful vinyl sulfones and sulfonamides are synthesized by the direct coupling of thiosulfonates with alkenes and amines, respectively. Copper catalysts help to generate the sulfonyl group from thiosulfonates and to form the C(sp2)–S/N–S bonds of the organosulfur compounds. This paper discusses the scope of these reactions of aromatic and aliphatic thiosulfonates with alkenes and amines.

Photocatalytic Oxidation of Sulfinates to Vinyl Sulfones with Cyanamide‐Functionalised Carbon Nitride

The cyanamide‐functionalised carbon nitride (NCN‐CNx) can be employed as a photo‐redox catalyst for the light‐induced sulfonylation of alkenes with sulfinate salts, attaining product yields twice those obtained with the non‐functionalised counterpart and comparable to those achieved with the benchmark homogeneous photocatalyst Eosin Y. NCN‐CNx as a heterogeneous photocatalyst is easily isolatable and can be re‐used for this reaction for over three cycles. This photocatalytic reaction can proceed with various sulfinates (aryl‐, alkyl‐ and thiophene‐based) and alkenes with electron‐donating and ‐withdrawing groups, obtaining good to excellent product yields. A reductive quenching route was determined to be the likely mechanism for this photocatalyst.

ChemInform Abstract: Ammonium Iodide‐Induced Sulfonylation of Alkenes with DMSO and Water Toward the Synthesis of Vinyl Methyl Sulfones.

AbstractThe novel and highly stereoselective sulfonylation of olefins with DMSO and H2O is achieved using NH4I as promoter to give vinyl methyl sulfones.

Palladium‐Catalyzed Desulfitative Mizoroki–Heck Couplings of Sulfonyl Chlorides with Mono‐ and Disubstituted Olefins: Rhodium‐Catalyzed Desulfitative Heck‐Type Reactions under Phosphine‐ and Base‐Free Conditions

New conditions have been found for the desulfitative Mizoroki-Heck arylation and trifluoromethylation of mono- and disubustituted olefins with arenesulfonyl and trifluoromethanesulfonyl chlorides. Thus (E)-1,2-disubstituted alkenes with high stereoselectivity and 1,1,2-disubstituted alkenes with 12:1 to 21:1 E/Z steroselectivity can be obtained. Herrmann's palladacycle at 0.1 mol % is sufficient to catalyze these reactions, for which electron-rich or electron-poor sulfonyl chlorides and alkenes are suitable. If phosphine- and base-free conditions are required, 1 mol % [RhCl(C(2)H(4))(2)] catalyzes the desulfitative cross-coupling reactions. Contrary to results reported for [RuCl(2)(PPh(3))(2)]-catalyzed coupling reactions with sulfonyl chlorides, the palladium and rhodium desulfitative Mizoroki-Heck coupling reactions are not inhibited by radical scavenging agents. Possible sulfones arising from the sulfonylation of alkenes at 60 degrees C are not desulfitated at higher temperatures in the presence of the Pd or Rh catalysts.