1125-25-3Relevant academic research and scientific papers
Nickel-Catalyzed Defluorinative Reductive Cross-Coupling Reaction of gem-Difluoroalkenes with Thiosulfonate or Selenium Sulfonate
Li, Jian,Rao, Weidong,Wang, Shun-Yi,Ji, Shun-Jun
, p. 11542 - 11552 (2019)
A nickel-catalyzed defluorinative reductive cross-coupling of gem-difluoroalkenes with thiosulfonate or selenosulfonates is described. The reaction involves the formation of thiolated or selenylated monofluoroolefins via regioselective C-F bond cleavage and C-S or C-Se bond formation and features easily available substrates, mild reaction conditions, and high E-selectivity. One of the derivatives by further cross coupling with PhMgBr exhibited an aggregation-induced emission enhancement effect.
Enzyme-catalysed oxidation of 1,2-disulfides to yield chiral thiosulfinate, sulfoxide and cis-dihydrodiol metabolites
Boyd, Derek R.,Sharma, Narain D.,Shepherd, Steven D.,Allenmark, Stig G.,Allen, Christopher C. R.
, p. 27607 - 27619 (2014)
Enantioenriched and enantiopure thiosulfinates were obtained by asymmetric sulfoxidation of cyclic 1,2-disulfides, using chemical and enzymatic (peroxidase, monooxygenase, dioxygenase) oxidation methods and chiral stationary phase HPLC resolution of racemic thiosulfinates. Enantiomeric excess values, absolute configurations and configurational stabilities of chiral thiosulfinates were determined. Methyl phenyl sulfoxide, benzo[c]thiophene cis-4,5-dihydrodiol and 1,3-dihydrobenzo[c]thiophene derivatives were among unexpected types of metabolites isolated, when acyclic and cyclic 1,2-disulfide were used as substrates for Pseudomonas putida strains. Possible biosynthetic pathways are presented for the production of metabolites from 1,4-dihydrobenzo-2,3-dithiane, including a novel cis-dihydrodiol metabolite that was also derived from benzo[c]thiophene and 1,3-dihydrobenzo[c]thiophene.
Visible-Light-Induced Radical Cascade Reaction of 1-Allyl-2-ethynylbenzoimidazoles with Thiosulfonates to Assemble Thiosulfonylated Pyrrolo[1,2-a]benzimidazoles
Liu, Yan,Zhang, Niuniu,Xu, Yanli,Chen, Yanyan
, p. 16882 - 16891 (2021/11/18)
A visible-light-induced radical domino reaction of 1-allyl-2-ethynylbenzoimidazoles with thiosulfonates was developed, which generated the thiosulfonylated pyrrolo[1,2-a]benzimidazoles in moderate to good yields. This reaction proceeded under transition-metal-free conditions with good functional group tolerance and high regioselectivity. The possible pathway involved thiosulfonates were activated through the energy transfer route promoted by photocatalysis.
Visible-Light-Induced Cyclization/Aromatization of 2-Vinyloxy Arylalkynes: Synthesis of Thio-Substituted Dibenzofuran Derivatives
Chen, Hui,Chen, Yanyan,Mo, Zuyu,Xu, Yanli,Yan, Yunyun,Zhang, Niuniu
supporting information, p. 376 - 381 (2021/01/13)
A visible-light-induced cascade reaction of 2-vinyloxy arylalkynes with thiosulfonates was developed and provided unexpected thio-substituted dibenzofuran derivatives in moderate yields. Mechanistic studies revealed the thiosulfonylation product of 2-vinyloxy arylalkyne was the key intermediate, and the additive disulfide played the role of hydrogen abstraction in the aromatization process to offer the desired product. This reaction presents a new reaction mode for the construction of polycyclic oxygen heterocycles.
Gold/photoredox-cocatalyzed atom transfer thiosulfonylation of alkynes: Stereoselective synthesis of vinylsulfones
Song, Tingting,Li, Haoyu,Wei, Fang,Tung, Chen-Ho,Xu, Zhenghu
supporting information, p. 916 - 919 (2019/02/27)
We report a gold and photoredox combined radical approach for the rapid synthesis of thio-functionalized vinylsulfones from alkynes. Key features of this method include very mild conditions, broad substrate scope, excellent regio- and stereoselectivties, and 100% atom economy.
Rh(ii)/phosphine-cocatalyzed synthesis of dithioketal derivatives from diazo compounds through simultaneous construction of two different C-S bonds
Rao, Changqing,Mai, Shaoyu,Song, Qiuling
supporting information, p. 5964 - 5967 (2018/06/18)
Rhodium(ii)/phosphine-cocatalyzed bis-sulfuration of α-diazocarbonyl compounds using thiosulfonates as the sulfenylating agent, which provided two sulfur-containing moieties, was developed via simultaneous inter- and intra-molecular C-S bond formation. This novel protocol provides a rapid synthetic route to dithioketal derivatives in moderate to good yields in an atom-economic process. The transformation is proposed to proceed through phosphine ylide formation followed by S(O2)-S bond cleavage and rearrangement.
Copper-Catalyzed Oxidative Trifunctionalization of Olefins: An Access to Functionalized β-Keto Thiosulfones
Huang, Shuai,Thirupathi, Nuligonda,Tung, Chen-Ho,Xu, Zhenghu
, p. 9449 - 9455 (2018/08/01)
Aerobic oxidative trifunctionalization of olefins for the synthesis of functionalized β-keto thiosulfones has been described. The transformation proceeds through molecular oxygen activation under copper catalysis and forms the two new C-S bonds in a single operation using mild conditions. A novel Cu-catalyzed sulfonyl radical addition/oxidation/funtionalization relay mechanism was proposed for the discovered reaction.
Alkynyl Thioethers in Gold-Catalyzed Annulations To Form Oxazoles
Reddy, Raju Jannapu,Ball-Jones, Matthew P.,Davies, Paul W.
supporting information, p. 13310 - 13313 (2017/10/07)
Non-oxidative, regioselective, and convergent access to densely functionalized oxazoles is realized in a functional-group tolerant manner using alkynyl thioethers. Sulfur-terminated alkynes provide access to reactivity previously requiring strong donor-substituted alkynes such as ynamides. Sulfur does not act in an analogous donor fashion in this gold-catalyzed reaction, thus leading to complementary regioselective outcomes and addressing the limitations of using ynamides.
Copper(I)-Catalyzed Interrupted Click Reaction: Synthesis of Diverse 5-Hetero-Functionalized Triazoles
Wang, Weiguo,Peng, Xianglong,Wei, Fang,Tung, Chen-Ho,Xu, Zhenghu
supporting information, p. 649 - 653 (2016/02/27)
The 5-heterofunctionalized triazoles are important scaffolds in bioactive compounds, but current click reactions (CuAAC) cannot produce these core structures. A copper(I)-catalyzed interrupted click reaction to access diverse 5-functionalized triazoles is reported. Various 5-amino-, thio-, and selenotriazoles were readily assembled in one step in high yields. The reaction proceeds under mild conditions with complete regioselectivity. It also features a broad substrate scope and good functional group compatibility.
METHOD FOR PRODUCING ORGANIC POLYSULFIDE COMPOUND AND ORGANIC POLYSULFIDE COMPOUND
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Paragraph 0075; 0077, (2018/10/31)
PROBLEM TO BE SOLVED: To provide a novel method for producing an organic polysulfide compound which can be used as a positive electrode substance. SOLUTION: A thiol compound represented by the formula (1) and having a plurality of thiol groups (-SH) and thiosulfonic ester represented by the formula(2) is mixed in presence of base to synthesize a disulfide compound having a structure represented by the formula (3) and the disulfide compound of the formula (3) is reacted with sulfur S8. This provides an organic polysulfide compound. A(-SH)a (1) B-S-SO2-C (2) A(-S-S-B)a (3), where A, B and C represent an organic group and a represents an integer of 2 or more. COPYRIGHT: (C)2015,JPOandINPIT
