- Visible-Light-Induced Radical Cascade Reaction of 1-Allyl-2-ethynylbenzoimidazoles with Thiosulfonates to Assemble Thiosulfonylated Pyrrolo[1,2-a]benzimidazoles
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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.
- Liu, Yan,Zhang, Niuniu,Xu, Yanli,Chen, Yanyan
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p. 16882 - 16891
(2021/11/18)
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- Direct conversion of sulfinamides to thiosulfonates without the use of additional redox agents under metal-free conditions
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Direct conversion of sulfinamides to thiosulfonates is described. Without the use of additional redox agents, the reaction proceeds smoothly in the presence of TFA under metal-free conditions. This protocol possesses many advantages such as odourless and stable starting materials, broad substrate scope, selective synthesis, and mild reaction conditions. This journal is
- Ji, Yuan-Zhao,Li, Hui-Jing,Wang, Jun-Hu,Wu, Yan-Chao,Zhang, Chi
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p. 9291 - 9298
(2021/11/13)
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- An iodine-mediated new avenue to sulfonylation employingN-hydroxy aryl sulfonamide as a sulfonylating agent
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A novel and highly efficient I2/K2CO3mediated regioselective sulfonylation of thiophenols, aryl acetylenic acid and aromatic alkynes withN-hydroxy sulfonamide has been developed.N-hydroxy sulfonamide has been used for the first time for the synthesis of these sulfones. The scope and versatility of the reaction has been demonstrated by the regio- and stereoselective synthesis of different analogs of sulfones with various structural features.
- Raghuvanshi, Dushyant Singh,Verma, Narsingh
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supporting information
p. 4760 - 4767
(2021/06/09)
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- Metal-Free Chemoselective Reaction of Sulfoxonium Ylides and Thiosulfonates: Diverse Synthesis of 1,4-Diketones, Aryl Sulfursulfoxonium Ylides, and β-Keto Thiosulfones Derivatives
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A diverse chemoselective insertion reaction of sulfoxonium ylides and thiosulfonates under transition-metal-free conditions is developed, which successfully affords 1,4-diketone compounds, arylthiosulfoxide-ylides, and β-keto thiosulfones, respectively. The nucleophilic addition of two molecular sulfoxonium ylides to construct sulfone-substituted 1,4-dione compounds is the highlight of this work.
- Wang, Fei,Liu, Bo-Xi,Rao, Weidong,Wang, Shun-Yi
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supporting information
p. 6600 - 6604
(2020/09/02)
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- Disproportionate Coupling Reaction of Sodium Sulfinates Mediated by BF3·OEt2: An Approach to Symmetrical/Unsymmetrical Thiosulfonates
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The BF3·OEt2-mediated disproportionate coupling reaction of sodium sulfinates was found for the first time. In this reaction, various S-S(O)2 bonds can be formed, efficiently giving thiosulfonates in moderate to excellent yields. As a convenient protocol for the synthesis of symmetrical and unsymmetrical thiosulfonates, its reaction mechanism involves the formation of a thiyl radical and sulfonyl radical via a sulfinyl radical disproportionation. What is more, this transformation can also be applied practically as a gram-scale reaction and to the two-step synthesis of sulfone and sulfonamide in one pot in situ using thiosulfonate as an intermediate.
- Cao, Liang,Luo, Shi-He,Jiang, Kai,Hao, Zhi-Feng,Wang, Bo-Wen,Pang, Chu-Ming,Wang, Zhao-Yang
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supporting information
p. 4754 - 4758
(2018/08/24)
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- Tunable and Practical Synthesis of Thiosulfonates and Disulfides from Sulfonyl Chlorides in the Presence of Tetrabutylammonium Iodide
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A tunable and practical synthesis of electrophilic sulfenylating reagents, thiosulfonates and disulfides, from inexpensive and easily available sulfonyl chlorides, has been developed. By appropriate choice of solvents, the reaction of sulfonyl chlorides and tetrabutylammonium iodide gave the target products in good to excellent yields, respectively. These transformations probably proceed through a reducing–coupling pathway. (Figure presented.).
- Zheng, Yong,Qing, Feng-Ling,Huang, Yangen,Xu, Xiu-Hua
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supporting information
p. 3477 - 3481
(2016/11/13)
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- Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates
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A new method for the synthesis of secondary thiocarbamates from readily available isocyanides and thiosulfonates with broad functional group tolerance is reported. The reaction proceeds under mild reaction conditions in isopropanol and is catalyzed by inexpensive sodium iodide.
- Mampuys, Pieter,Zhu, Yanping,Sergeyev, Sergey,Ruijter, Eelco,Orru, Romano V. A.,Van Doorslaer, Sabine,Maes, Bert U. W.
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supporting information
p. 2808 - 2811
(2016/07/06)
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- Sc(OTf)3-catalyzed synthesis of thiosulfonates in ionic liquid-water
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The first example of Sc(OTf)3-catalyzed sulfenylation of sodium sulfinates with N-(organothio)succinimides in ionic liquids (ILs) and water cosolvent system was developed, achieving thiosulfonates in moderate to excellent yields. Additionally, Sc(OTf)3/ILs could be recovered easily after the reactions and reused without a significant loss in the catalytic activity. Thus, the present protocol represents an interesting complement to known methods for thiosulfonates synthesis.
- Liang, Gaigai,Chen, Jing,Chen, Jiali,Li, Wanmei,Chen, Jiuxi,Wu, Huayue
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supporting information
p. 6768 - 6770
(2013/01/15)
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- A new synthesis of cytotoxic thiosulfonates and the first synthesis of deuterated thiosulfonates
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A new synthesis of thiosulfonates starting from thiophenols and cyanuric chloride activated dimethyl sulfoxide is reported herein. Although the yields of the reactions are moderate, this method enables the incorporation of the SCD3 group of dimethyl sulfoxide-d6 into thiosulfonates. This is the first synthesis of deuterated thiosulfonates with a labeling purity above 99%. In addition, the cytotoxicity of the thiosulfonates is reported for the first time. Georg Thieme Verlag Stuttgart. New York.
- Gao, Feng,Zhai, Huiyuan,Jin, Meina,Chu, Guobiao,Duan, Hongquan,Li, Chunbao
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experimental part
p. 3635 - 3638
(2011/12/16)
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- Antifungal thiosulfonates: Potency with some selectivity
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A series of thiosulfonates have been prepared and tested against Aspergillus niger and Aspergillus flavus. In general, the thiosulfonates are moderate antifungal agents - more potent than corresponding inactive disulfides and less potent than corresponding very active fungitoxic disulfides. A pair of thiosulfonates show high selectivity, each killing only one kind of fungus. CSIRO 2000.
- Baerlocher, Felix Jakob,Baerlocher, Mark Otto,Chaulk, Crystal Lee,Langler, Richard Francis,MacQuarrie, Stephanie Lee
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p. 399 - 402
(2007/10/03)
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- S-Alkyl Alkanesulfonothioates and S-1-Chloroalkyl Alkanesulfonothioates from Linear Alkanesulfinyl Chlorides
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Treatment of linear alkanesulfinyl chlorides 1 with dry N,N-dimethylmethanamide (DMF), N,N-dimethylethanamide (DMA), or 1-methyl-2-pyrrolidone (NMP) in an inert atmosphere, with or without added solvent, gives S-alkyl alkanesulfonothioates 4 (minor products) and S-1-chloroalkyl alkanesulfonothioates 5.The yield of 4 is decreased in the presence of the radical inhibitor 1,4-dihydroxybenzene.Evidence has been obtained for the formation and trapping of sulfines (including methanethial S-oxide) and for formation of sulfinyl radicals, vic-disulfoxides (α-disulfoxides), and O,S-sulfenyl sulfinates as reaction intermediates.S-Phenyl benzenesulfonothioate is a major product from the reaction of alkanesulfinyl chlorides and benzenesulfinyl chloride in the presence of DMF.
- Freeman, Fillmore,Keindl, Monica C.
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p. 2026 - 2031
(2007/10/02)
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- Oxidation of Unsymmetrical Disulfide and Thiosulfinic S-Esters with Peroxy Acids. Search for Formation of α-Disulfoxide as An Intermediate in the Electrophilic Oxidation of Thiosulfinic S-Ester
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Oxidation of an unsymmetrical disulfide, methyl phenyl disulfide, with peroxy acids takes place mainly at more electron-rich sulfur atom to form thiosulfinic S-ester at the first stage, while oxidation of unsymmetrical thiosulfinic S-ester with peroxy acids gives usually four thiosulfonic S-esters, together with sulfinic and sulfonic acids, further oxidation products.Oxidation of S-methyl benzenethiosulfinate 6 affords, as one of the products, S-phenyl methanethiosulfonate 11, in which the original sulfinyl oxygen is brought into methanesulfonyl group.A small amount of S-phenyl benzenethiosulfonate 9 (or benzenesulfonic acid 15) is obtained in the oxidation of S-phenyl methanethiosulfinate 7. 18O-Label of the starting thiosulfinic S-ester 6 was found to be incorporated to some extents into all four products, i.e. 8-11, while a part of 18O-label of S-phenyl methanethiosulfinate 7 was also observed in S-phenyl benzenethiosulfonate 9 and benzensulfonic acid 15, although most of 18O-label of 7 was incorporated into S-phenyl methanethiosulfonate 11.Thiosulfinic S-esters are stable and do not undergo disproportionation and 18O-exchange under the conditions.These observations suggest the formation of α-disulfoxide as an intermediate in the oxidation of thiosulfinic S-ester to thiosulfonic S-ester, especially in the oxidation of 6, although no peak corresponding to α-disulfoxide was observed directly in the NMR spectra taken during the oxidations of a few thiosulfinic S-esters with peroxy acid.Mechanism of the oxidation is discussed.
- Oae, Shigeru,Takata, Toshikazu,Kim, Yong Hae
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p. 2484 - 2494
(2007/10/02)
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- Selective Oxidation of Unsymmetrical Thiosulfinic S-Esters to the Corresponding Thiosulfonic S-Esters with NaIO4
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Unsymmetrical thiosulfinic S-esters were oxidized with sodium metaperiodate in aqueous media to the corresponding unsymmetrical thiosulfonic S-esters nearly quantitatively.The oxidation was accelerated by addition of a catalytic amount of inorganic and organic acids or halogen.Sulfinic esters were produced competitively along with the thiosulfonic S-esters in the oxidation of thiosulfinic S-esters in aqueous alcohol.However, unsymmetrical disulfides were not oxidized selectively to the corresponding unsymmetrical thiosufonic S-esters but a mixture of the both symmetrical and unsymmetrical thiosulfonic S-esters was obtained.
- Takata, Toshikazu,Kim, Yong Hae,Oae, Shigeru
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p. 1443 - 1447
(2007/10/02)
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