- KI-catalyzed synthesis of S-Thiocarbamates by cross-coupling of cyclohexyl isocyanide with sulfonyl chlorides
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A simple and efficient process for direct generation of various S-thiocarbamates is developed by cross-coupling of readily available sulfonyl chlorides with cyclohexyl isocyanide. The yields are excellent and the structures of the generated S-thiocarbamat
- Lin, Liangwei,Fang, Zhengjun,Li, Yajun,Wu, Feng,Au, Chaktong,Luo, Sai
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- 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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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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- 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 0037; 0038
(2019/04/04)
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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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- 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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- Thermolysis-Induced Two- or Multicomponent Tandem Reactions Involving Isocyanides and Sulfenic-Acid-Generating Sulfoxides: Access to Diverse Sulfur-Containing Functional Scaffolds
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Direct reaction of isocyanides with some sulfenic-acid-generating sulfoxides led to the effective formation of the corresponding thiocarbamic acid S-esters in good to high yields. A multicomponent reaction involving isocyanide, sulfoxide, and a suitable nucleophile has also been developed, providing ready access to a diverse range of sulfur-containing compounds, including isothioureas, carbonimidothioic acid esters, and carboximidothioic acid esters.
- Wu, Shengfeng,Lei, Xiaofang,Fan, Erkang,Sun, Zhihua
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p. 522 - 525
(2018/02/10)
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- One-pot synthesis of carbamates and thiocarbamates from Boc-protected amines
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A highly efficient one-pot procedure for the synthesis of carbamates and thiocarbamates has been described. In the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, the isocyanate intermediates were generated in situ for further reactions with alcohols and thiols to afford the desired carbamates and thiocarbamates in high yields.
- Kim, Hee-Kwon,Lee, Anna
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p. 4890 - 4892
(2016/10/21)
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- Facile one-pot synthesis of unsymmetrical ureas, carbamates, and thiocarbamates from Cbz-protected amines
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A novel one-pot synthesis of unsymmetrical ureas, carbamates and thiocarbamates from Cbz-protected amines has been developed. In the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, isocyanates are generated in situ, which facilitate rapid reaction with amines, alcohols, and thiols to afford the corresponding ureas, carbamates and thiocarbamates in high yields.
- Kim, Hee-Kwon,Lee, Anna
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supporting information
p. 7345 - 7353
(2016/08/05)
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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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p. 2808 - 2811
(2016/07/06)
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- Thiol-isocyanate-ene ternary networks by sequential and simultaneous thiol click reactions
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Thiol-isocyanate-ene ternary networks with systematic variations (100/100/0, 100/80/20, 100/60/40, 100/40/60, 100/20/80, and 100/0/100) were prepared by sequential and simultaneous thiol-ene and thiol-isocyanate click reactions. The thiol-isocyanate coupling reaction was triggered thermally or photolytically to control the sequence with the thiol-ene photopolymerization. Triethyl amine (TEA) and 2,2-dimethoxy-2-phenyl acetophenone (DMPA) were used for the sequential thermally induced thiol-isocyanate coupling and photochemically initiated thiol-ene reaction, respectively. A thermally stable photolatent base catalyst (tributylaminetetraphenylborate salt, TBAHBPh 4) capable of in situ generation of tributylamine by UV light was used with isopropylthioxanthone (ITX) for the simultaneous thiol-isocyanate/ thiol-ene curing systems. The kinetics of the hybrid networks investigated using real-time IR indicate that both thiol-isocyanate and thiol-ene reactions were quantitatively rapid and efficient (>90% of conversion in a matter of minutes and seconds, respectively). The Tg of the thiourethane/thiol-ene hybrid networks progressively increases (-5 to 35 °C by DSC) as a function of the thiourethane content due to the higher extent of hydrogen bonding, also resulting in enhanced mechanical properties. Highly uniform and dense network structures exhibiting narrow full width at half-maximum (~10 °C) were obtained for both the sequential and the simultaneous thiol click reactions, resulting in identical thermal properties that are independent of the sequence of the curing processes.
- Shin, Junghwan,Matsushima, Hironori,Comer, Christopher M.,Bowman, Christopher N.,Hoyle, Charles E.
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scheme or table
p. 2616 - 2625
(2011/11/13)
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- Synthesis of thiocarbamates from thiols and isocyanates under catalyst- and solvent-free conditions
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A simple and efficient procedure was developed for the synthesis of S-alkyl (aryl) thiocarbamates under solvent-free conditions without the use of a catalyst. The significant features of this protocol are (a) operational simplicity, (b) mild reaction cond
- Movassagh, Barahman,Soleiman-Beigi, Mohammad
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p. 137 - 140
(2008/09/20)
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