- Visible-light-promoted synthesis of secondary and tertiary thiocarbamates from thiosulfonates andN-substituted formamides
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A general visible-light-promoted metal-free synthesis of secondary and tertiary thiocarbamates starting from thiosulfonates andN-substituted formamides is developed. By employing rhodamine B as a photocatalyst andtert-butyl hydroperoxide (TBHP) as an oxidant, a wide scope of thiocarbamates can be obtained through direct thiolation of acyl C-H bonds under irradiation of blue light at room temperature for 12 h.
- Bi, Wen-Zhu,Zhang, Wen-Jie,Li, Zi-Jie,He, Yuan-Hao,Feng, Su-Xiang,Geng, Yang,Chen, Xiao-Lan,Qu, Ling-Bo
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supporting information
p. 8701 - 8705
(2021/10/22)
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- Electrochemical metal- And oxidant-free synthesis of S-thiocarbamates
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An expeditious synthetic strategy to access functionalized S-thiocarbamates was developed in good to excellent yields and with high current efficiencies. Readily available isocyanides and thiols were used as the starting materials under simple metal- and oxidant-free reaction conditions avoiding an inert atmosphere. The practical application of the present methodology was achieved by electrochemical synthesis of the herbicides prosulfocarb and pebulate. Furthermore, continuous electrochemical flow conditions using a graphite/Pt flow cell were used to obtain S-thiocarbamate compounds on a gram scale within a residence time of 35 min. This journal is
- Malviya, Bhanwar Kumar,Sharma, Siddharth,Verma, Ved Prakash
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p. 9491 - 9500
(2021/11/17)
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- Synthesis of carbamothioate derivatives via a copper catalyzed thiocarboxamidation of aryl iodides
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Abstract: A catalytic route to carbamothioate derivatives through a reaction involving isocyanides, elemental sulfur, and aryl iodides has been developed. The reaction scope has been examined using a range of isocyanides and aryl iodides. The reactions involve two consecutive C–S bond formations. Control experiment revealed that the reaction proceeds through an iminium species. Graphic abstract: [Figure not available: see fulltext.].
- Khalaj, Mehdi
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p. 945 - 952
(2020/05/26)
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- Clean preparation of S-thiocarbamates with in situ generated hydroxide in 2-methyltetrahydrofuran
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A simple and clean protocol for the synthesis of various alkyl and (hetero)aryl S-thiocarbamates was established. The usage of in situ generated hydroxide as both an oxygen source and hydrogen source as well as biomass-derived 2-methyltetrahydrofuran as a
- Bao, Wen-Hu,Wang, Zheng,Tang, Xiao,Zhang, Yun-Fu,Tan, Jia-Xi,Zhu, Qin,Cao, Zhong,Lin, Ying-Wu,He, Wei-Min
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supporting information
p. 2259 - 2262
(2019/07/30)
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- Visible-light mediated sulfonylation of thiols via insertion of sulfur dioxide
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A simple and efficient visible-light mediated synthesis of thiosulfonates via a radical-radical coupling of sulfenyl radicals and arylsulfonyl radicals was developed. The reaction of thiols, aryldiazonium tetrafluoroborates and DABSO proceeded at room temperature using 5 mol% eosin Y. The reaction displayed wide functional group tolerance and delivered the unsymmetrical thiosulfonates in good to excellent yields.
- Nair, Akshay M.,Kumar, Shreemoyee,Halder, Indranil,Volla, Chandra M. R.
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p. 5897 - 5901
(2019/06/24)
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- Iodine-Catalyzed Odorless Synthesis of S-Thiocarbamates with Sulfonyl Chlorides as a Sulfur Source
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A general and efficient protocol for the direct preparation of various S-thiocarbamates with readily available and inexpensive sulfonyl chlorides as an odorless sulfur source was developed. The employment of easily available reactants, excellent functiona
- Bao, Wen-Hu,He, Min,Wang, Jing-Ting,Peng, Xin,Sung, Men,Tang, Zilong,Jiang, Si,Cao, Zhong,He, Wei-Min
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p. 6065 - 6071
(2019/05/24)
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- Metal-Free Catalytic Synthesis of Thiocarbamates Using Sodium Sulfinates as the Sulfur Source
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A novel molecular iodine-catalyzed protocol for the construction of thiocarbamates from readily available sodium sulfinates, isocyanides, and water has been described. The present methodology offers a facile and practical route to a variety of thiocarbamates in moderate to good yields with favorable functional group tolerance by use odorless sodium sulfinates as the sulfur source. The mechanistic studies suggest the present transformation involves a radical process.
- Bao, Pengli,Wang, Leilei,Yue, Huilan,Shao, Yun,Wen, Jiangwei,Yang, Daoshan,Zhao, Xiaohui,Wang, Hua,Wei, Wei
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p. 2976 - 2983
(2019/03/07)
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- Preparation method of thiocarbamate compound
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The invention belongs to the field of synthesis of a compound, relates to a preparation method of a thiocarbamate compound, in particular to a method for synthesizing thiocarbamate through reacting ofcatalyzing three components of sodium sulfinate, isonitrile and water by iodine. The method comprises the following steps: adding the sodium sulfinate, the isonitrile and the water into ethyl acetate, then adding a molecular iodine catalyst and a phosphite reducing agent, heating, stirring and reacting for 6 to 10 hours under a condition that the temperature is 80 to 100 DEG C, and extracting, separating and purifying after finishing the reaction, thus obtaining the thiocarbamate. According to the method disclosed by the invention, the isonitrile is adopted as a carbon source, so that poisonous photogene and carbon monoxide are prevented from being used; odorless sodium sulfinate is adopted as a sulfur source, so that odorous thiophenol or thiol is prevented from being used; non-metalliciodine is adopted for catalyzing, so that a metal reagent is prevented from being used; the reaction has the advantages that the operation is simple and convenient, the technology is safe, environmentfriendliness is realized, and the like.
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Paragraph 0041; 0042
(2019/04/04)
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- Iodine-catalyzed cross-coupling of isocyanides and thiols for the synthesis of: S -thiocarbamates
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A novel and efficient metal free, redox-neutral method for the synthesis of secondary thiocarbamates by cross-coupling of readily available thiophenol and isocyanides has been developed. The present methodology exhibits a broad substrate scope with good to excellent yields without an additive/extra oxidant under mild reaction conditions catalyzed by inexpensive iodine as the catalyst.
- Pathare, Ramdas S.,Patil, Vikas,Kaur, Harpreet,Maurya, Antim K.,Agnihotri, Vijai K.,Khan, Shahnawaz,Devunuri, Nagaraju,Sharon, Ashoke,Sawant, Devesh M.
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supporting information
p. 6885 - 6888
(2018/10/02)
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- Molecular iodine-mediated synthesis of thiocarbamates from thiols, isocyanides and water under metal-free conditions
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A simple and practical molecular iodine-mediated method for the efficient construction of thiocarbamates from isocyanides, thiols and water under metal-free and mild conditions has been developed. A variety of thiocarbamates were easily synthesized through this methodology, which has the advantages of simple operation, eco-friendly conditions, good functional group tolerance, and readily accessible raw materials.
- Bao, Wen-Hu,Wu, Chao,Wang, Jing-Ting,Xia, Wen,Chen, Ping,Tang, Zilong,Xu, Xinhua,He, Wei-Min
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supporting information
p. 7025 - 7029
(2018/10/02)
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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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