- An iodine-mediated new avenue to sulfonylation employingN-hydroxy aryl sulfonamide as a sulfonylating agent
-
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
-
supporting information
p. 4760 - 4767
(2021/06/09)
-
- Tunable and Practical Synthesis of Thiosulfonates and Disulfides from Sulfonyl Chlorides in the Presence of Tetrabutylammonium Iodide
-
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
-
supporting information
p. 3477 - 3481
(2016/11/13)
-
- Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates
-
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.
-
supporting information
p. 2808 - 2811
(2016/07/06)
-
- Sustainable three-component synthesis of isothioureas from isocyanides, thiosulfonates, and amines
-
Multiple applications of isothioureas as fine chemicals (or their precursors) are known, but a general sustainable method for their synthesis was hitherto unavailable. We report a novel general approach towards S-alkyl and S-aryl isothioureas through a copper(I)-catalyzed three-component reaction between amines, isocyanides, and thiosulfonates. The formal synthesis of a superpotent sweetener further illustrates the applicability of our method. Safety first! A direct synthesis of isothioureas by a copper-catalyzed three-component reaction from readily available substrates (see scheme) avoids the toxic, flammable, and highly reactive reagents required in classical approaches. The reaction also enables the straightforward synthesis of S-aryl isothioureas, which are difficult to obtain by other methods.
- Mampuys, Pieter,Zhu, Yanping,Vlaar, Tj?stil,Ruijter, Eelco,Orru, Romano V. A.,Maes, Bert U. W.
-
supporting information
p. 12849 - 12854
(2016/02/18)
-
- 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. Copyright
- Liang, Gaigai,Liu, Miaochang,Chen, Jiuxi,Ding, Jinchang,Gao, Wenxia,Wu, Huayue
-
experimental part
p. 1611 - 1616
(2012/09/07)
-
- A new synthesis of cytotoxic thiosulfonates and the first synthesis of deuterated thiosulfonates
-
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
-
experimental part
p. 3635 - 3638
(2011/12/16)
-
