54696-23-0Relevant academic research and scientific papers
Transition Metal-Free C-H Thiolation via Sulfonium Salts Using β-Sulfinylesters as the Sulfur Source
Chen, Yanhui,Wen, Si,Tian, Qingyu,Zhang, Yuqing,Cheng, Guolin
supporting information, p. 7905 - 7909 (2021/10/20)
We disclose a direct C(sp)-, C(sp2)-, and C(sp3)-H thiolation reaction using β-sulfinylesters as the versatile sulfur source. The key step of this protocol is chemoselective C-S bond cleavage of the sulfonium salts that are formed in situ from the corresponding alkenes, alkynes, and 1,3-dicarboxyl compounds with β-sulfinylesters. The successful capture of the acrylate byproduct supports a retro-Michael reaction mechanism.
Microwave-Assisted Pd-Catalyzed Desulfitative C-S Coupling of Arylsulfinate Metal Salts and Alkanethiols
Li, Junchen,Bi, Xiaojing,Wang, Hongmei,Xiao, Junhua
, p. 1873 - 1881 (2015/11/02)
This paper reports a palladium-catalyzed C-S coupling of arylsulfinate metal salts and alkanethiols via liberation of sulfur dioxide. The use of PdCl2 as the catalyst in combination with AgNO3 as the oxidant under microwave irradiation results in the synthetically and biologically important aryl alkyl sulfides. A variety of arylsulfinate metal salts, such as sodium, potassium, lithium, silver, zinc, and copper salts, are tolerated well in this reaction.
Synthesis and biological evaluation of some new 2,5-disubstituted 1,3,4-oxadiazoles from 3-(arylsulfonyl) propanehydrazides
Vinay Kumar,Jagan Naik,Naveen,Chandrasekhar,Babul Reddy,Penchalaiah,Narayana Swamy
, p. 208 - 211 (2014/03/21)
Methyl acrylate on treatment with aryl thiols gives methyl 3-(arylthio) propanoates. The latter on oxidation with hydrogen peroxide followed by reaction with hydrazine hydrate gives 3-(arylsulfonyl) propanehydrazides. Two new series of 2,5-disubstituted-1
Rongalite and base-promoted cleavage of disulfides and subsequent Michael addition to α,β-unsaturated ketones/esters: an odorless synthesis of β-sulfido carbonyl compounds
Guo, Wenxue,Lv, Guangshu,Chen, Jiuxi,Gao, Wenxia,Ding, Jinchang,Wu, Huayue
supporting information; experimental part, p. 2297 - 2300 (2010/06/16)
A highly practical method to access β-sulfido carbonyl compounds was developed, which could be conducted without any expensive reagent, special apparatus/technique, and no requirement of metal catalysts. β-Sulfido carbonyl compounds were formed at room temperature, in short time and with high chemoselectivity in good to excellent yields. A plausible mechanism for the role of Rongalite, as a promoter for the cleavage of disulfides generating thiolate anions that then undergo facile thia-Michael addition to α,β-unsaturated ketones and esters is proposed.
Efficient synthesis of β-alkyl/arylsulfanyl carbonyl compounds by In-TMSCl-promoted cleavage of dialkyl/diaryl disulfides and subsequent Michael addition
Ranu, Brindaban C.,Mandal, Tanmay
, p. 1517 - 1523 (2008/02/03)
A convenient and efficient procedure for the synthesis of β-alkyl/arylsulfanyl carbonyl compounds has been developed by a simple one-pot reaction of dialkyl/diaryl sulfides with α,β-unsaturated aldehydes, ketones, carboxylic esters, and nitriles in presence of indium and trimethylsilyl chloride under sonication. Copyright Taylor & Francis Group, LLC.
Indium(I) iodide promoted cleavage of dialkyl disulfides - Application of the Michael addition of thiolate anions to conjugated carbonyl compounds and regioselective ring opening of epoxides
Ranu, Brindaban C.,Mandal, Tanmay
, p. 762 - 770 (2007/10/03)
Indium(I) iodide promotes cleavage of dialkyl disulfides generating thiolate anions that then undergo facile addition to α,β-unsaturated ketones, aldehydes, carboxylic esters, and nitriles under neutral conditions producing corresponding β-ketosulfides or β-cyanosulfides. This strategy has also been used for the regioselective nucleophilic ring opening of epoxides by thiolate anions in presence of indium(III) chloride producing corresponding β-hydroxyphenyl sulfides. The reactions are in general, very clean, high yielding, and reasonably fast. Thus, simple and convenient procedures for the synthesis of β-ketosulfides or β-cyanosulfides and β-hydroxyalkyl sulfides have been developed using this cleavage reaction.
Study of the Michael addition of β-cyclodextrin-thiol complexes to conjugated alkenes in water
Krishnaveni, N. Srilakshmi,Surendra,Rao, K. Rama
, p. 669 - 671 (2007/10/03)
An environmentally benign and highly efficient supramolecular Michael addition of thiols from the secondary side of β-cyclodextrin to α,β-unsaturated compounds at the primary side in water is described in quantitative yields; products of undesirable side
A simple and green procedure for the conjugate addition of thiols to conjugated alkenes employing polyethylene glycol (PEG) as an efficient recyclable medium
Kamal, Ahmed,Reddy, D. Rajasekhar,Rajendar
, p. 7951 - 7953 (2007/10/03)
Polyethylene glycol (PEG) is found to be an inexpensive, nontoxic, environmentally friendly reaction medium for the conjugate addition of thiols to conjugated alkenes to afford the corresponding adducts in excellent yields under mild and neutral condition
Chemical partitioning agents and methods of using same
-
Page column 24-25, (2010/02/05)
The present invention is directed to partitioning agents and methods of using same to effectuate separation of a reactant, intermediate product, and/or final product from a reaction mixture while minimizing the need for traditional separation or isolation techniques.
Indium(I) iodide-promoted cleavage of dialkyl disulfides and subsequent Michael addition of thiolate anions to conjugated carbonyl compounds
Ranu, Brindaban C.,Mandal, Tanmay
, p. 1239 - 1242 (2007/10/03)
Indium(I) iodide promotes cleavage of dialkyl disulfides generating thiolate anions which then undergo facile addition to α,β-unsaturated ketones, aldehydes, carboxylic esters and nitriles under neutral conditions producing corresponding β-keto or β-cyano
