TsCl-promoted sulfonylation of quinoline N-oxides with sodium sulfinates in water

An eco-friendly protocol for the synthesis of various 2-sulfonyl quinolines/pyridines through sulfonylation of heteroaromatic N-oxides with sodium sulfinates in water at ambient temperature under metal-and oxidant-free conditions has been developed.The mild reaction conditions,high reaction efficiency,operational simplicity,short reaction time and remarkable functional-group compatibility make the developed protocol very attractive for the preparation of 2-sulfonyl N-heteroaromatic compounds.

Direct C(sp^(3))-H Sulfonylation of Xanthene Derivatives with Sodium Sulfinates by Oxidative Copper Catalysis

By employing a readily available CuCI/DDQ catalyst system,we herein report a direct C(sp^(3))-H sulfonylation of xanthene derivates with odorless sodium sulfinates.Various 9H-xanthenes,thioxanthenes,and 9,10-dihydroacridines are efficiently transformed into the desired benzylic sulfonyl products via a radical/radical cross-coupling process,proceeding with the merits of broad substrate scope,operational simplicity,good functional group compatibility,and mild reaction conditions.

Electrosynthesis of Arylsulfonamides from Amines and Sodium Sulfinates Using H2O-Nal as the Electrolyte Solution at Room Temperature

With H2O as the solvent and NaI as the supporting electrolyte, a green and efficient electrochemical route has been developed to synthesize arylsulfonamides via I2 electrogenerated in situ at a graphite anode to promote the reaction of sodium sulfinates with aromatic or aliphatic primary and secondary amines. The target products could be obtained in good to excellent yields at room temperature.

A Mild and Rapid Synthesis of （Z）-β-Sulfonyl Enoates from Sodium Sulfinates and Propargyl Esters

Water-promoted sulfonylation of propargyl esters leading to highly regioselective and stereoselective formation of （Z）-β-sulfonyl enoates in excellent yields, by a simple, mild, rapid and environmentally benign reaction proce- dure is reported.

NBS-Promoted Sulfenylation of Sulfinates with Disulfides Leading to Unsymmetrical or Symmetrical Thiosulfonates

A highly practical method to access unsymmetrical and symmetrical thiosulfonates in moderate to excellent yields has been developed through NBS-promoted sulfenylation of sulfinates with disulfides. The present process enables the use of two RS in RSSR and shows broad functional group tolerance, which represents an atom-economical and practical procedure for the synthesis of thiosulfonates. A plausible mechanism for the role of NBS as a promoter for the cleavage of disulfides generating N-（organothio）succinimide that then undergos facile sulenylation with sulfinates is proposed.

Metal Free Mono- and 2,3-Bis-sulfenylation of Indoles in Water with Sodium Sulfinates as a Sulfur Source

An iodine-PPh3 mediated sulfenylation of indoles in water with stable and odorless sodium sulfinates as the sulfur source is described. The reaction could afford monosulfenylated indoles in moderate to excellent yields under metal free conditions. Moreover, double C--H sulfenylation of in- doles at 2- and 3-positions has also been achieved by using excess sodium sulfinates under the optimized reaction conditions.

Iodine-catalyzed N-sulfonylation of benzotriazoles with sodium sulfinates under mild conditions

A new and convenient procedure is developed for the preparation of N-sulfonylbenzotriazoles from sodium sulfinates and benzotriazoles using molecular iodine as catalyst via the S-N bond formation reaction. This catalytic radical sulfonylation proceeds efficiently in air at room temperature under neutral conditions, and in short reaction time, to afford the corresponding N-sulfonylbenzotriazoles in good yields, thus extending the catalytic application of molecular iodine in organic synthesis.

Visible-light-induced deoxygenative C2-sulfonylation of quinoline N-oxides with sulfinic acids for the synthesis of 2-sulfonylquinoline via radical reactions

A simple and efficient method for the synthesis of 2-sulfonylquinoline from deoxygenative C2-sulfonylation of quinoline N-oxides with sulfinic acid induced by visible light is presented.This protocol shows a broad substrate scope,and desired products with various substituents can be formed in moderate to high yields at room temperature.

DYSFUNCTION OF MYOCARDIAL AND VASCULAR TAURINE TRANSPORT IN L-N~ω-NITRO-ARGININE-INDUCED HYPERTENSIVE RATS

Objective.To study the change of taurine transport,and taurine transporter(TAUT)and cysteine sulfinate decarboxylase(CSD)mRNA contents in hypertension and hypertensive cardiomegaly.Methods.Taurine content was determined with a amino acid analyser.Taurine uptakes were deter-mined by( 3 H)-taurine incubation.The content of TAUT and CSD mRNA levels were measured by com-petitive quantitative RT-PCR in myocardial and vascular tissues of L-N ω -nitro-arginine(L-NNA)-in-duced hypertensive rats.Results.After the treatment of rats with L-NNA for28days,myocardial and vascular taurine con-tents decreased by11%and15%(P<0.05),respectively,and plasma taurine level increased by13%(P<0.05).Myocardial and vascular Vmax of taurine uptake reduced by30%and19%(P<0.05),respec-tively.Their Km of taurine uptake increased by36%and17%(P<0.05).Myocardial and vascular TAUT mRNA content decreased by22%and19%(P<0.05),respectively,but CSD mRNA content increased by22%(P<0.05)and30%(P<0.01),respectively.Conclusions.This study suggests that there is a decreased taurine content in myocardial and vascu-lar tissues of L-NNA-induced hypertension rats.The decreased taurine content may result from the de-creased number of TAUT on the cell membrane mainly due to the down-regulation of TAUT gene and TAUT affinity caused by hypertension and hypertensive cardiomegaly.

A Convenient Synthesis of β-Ketosulfoxides

β-Ketosulfoxides were synthesized by the reaction of acetone with aryl sulfinate esters in the presence of hydrochloric acid and the structure of title compounds were finally confirmed by IR.~1HNMR and ^(13)CNMR spectra.

Study on the sulfinatodehalogenation of BrCF_2CF_2R

Sodium dithionite initiated sulfinatodehalogenation of BrCF2CF2R is studied.

Copper-Mediated Di- and Monofluoromethanesulfonylation of Arenediazonium Tetrafluoroborates： Probing the Fluorine Effect

A copper-mediated di- and monoffuoromethanesulfonylation of arenediazonium tetrafluoroborates using di- and monofluoromethanesul- finate reagents provides aryl difluoromethyl （or monofluoromethyl） sulfones in 8ood yields. It was found that the relative reactivity of these sodium fluoroalkanesulfinates in the present reactions decreases in the followin8 order： CH2FSO2Na 〉 CF2HSO2Na 〉 CF3SO2Na.

Recent advances in the application of sulfinic acids for the construction of sulfur-containing compounds

Sulfur-containing organic compounds display wide applications in the field of materials science,synthetic chemistry,and pharmaceutical industry.Thus,numerous synthetic strategies have been developed for the synthesis of sulfur-containing compounds in synthetic chemistry.In recent years,the utilization of sulfinic acids as versatile synthons has emerged as attractive and powerful approach to access various organosulfur compounds through sulfonylation,sulfinylation or sulfenylation reactions.In this review,we summarized the recent progress in the construction of various sulfur-containing compounds from sulfininc acids.Selected examples of substrates and the related reaction mechanisms are described here.This review intends to provide readers a comprehensive understanding on the synthesis of sulfur-containing molecules from sulfinic acids and provide help for future synthetic research.

Electrochemical Synthesis of Sulfonyl Fluorides with Triethylamine Hydrofluoride

Hydrofluoride is an industry-preferred fluoride source,and finds extensively application to manufacture diverse fluoro chemicals.The Et3N-3HF complex is a liquid HF with improve safety.In this work,we report electrochemical synthesis of a series of sulfonyl fluoride with Et3N-3HF as fluoride source.The sulfinic salt is a smell-less,non-volatile,and air-stable sulfur source in this reaction.With the combination of Et3N-3HF and aryl/alkyl sulfinic salt,the sulfonyl fluorides are achieved without the use of external oxidant.In addition,we demonstrate further advantage in a tandem reaction involving Pd-catalyzed C—S cross-coupling and formation of S—F bond.A variety of functional groups including amino acids,heterocycles,halides are well tolerated.

Visible-light induced cascade radical cyclization of sulfinic acids and o-(allyloxy)arylaldehydes towards functionalized chroman-4-ones

An efficient method for the synthesis of functionalized chroman-4-ones induced by visible light via the radical cyclization reaction of sulfinic acids and o-(allyloxy)arylaldehydes at room temperature was described.The corresponding products were isolated with moderate to good yields.Radical mechanism was proposed fo r this trans formation.Anti-microbial activity of some desired compounds we re screened.