5331-36-2Relevant academic research and scientific papers
Nanolayered cobalt-molybdenum sulphides (Co-Mo-S) catalyse borrowing hydrogen C-S bond formation reactions of thiols or H2S with alcohols
Corma, Avelino,Sorribes, Iván
, p. 3130 - 3142 (2019/03/13)
Nanolayered cobalt-molybdenum sulphide (Co-Mo-S) materials have been established as excellent catalysts for C-S bond construction. These catalysts allow for the preparation of a broad range of thioethers in good to excellent yields from structurally diverse thiols and readily available primary as well as secondary alcohols. Chemoselectivity in the presence of sensitive groups such as double bonds, nitriles, carboxylic esters and halogens has been demonstrated. It is also shown that the reaction takes place through a hydrogen-autotransfer (borrowing hydrogen) mechanism that involves Co-Mo-S-mediated dehydrogenation and hydrogenation reactions. A novel catalytic protocol based on the thioetherification of alcohols with hydrogen sulphide (H2S) to furnish symmetrical thioethers has also been developed using these earth-abundant metal-based sulphide catalysts.
An atom-economic and odorless thia-Michael addition in a deep eutectic solvent
Azizi, Najmedin,Yadollahy, Zahra,Rahimzadeh-Oskooee, Amin
, p. 1722 - 1725 (2014/03/21)
The first 100% atom-efficient and odorless protocol for carbon-sulfur bond formation in a deep eutectic solvent (DES) as both the reaction medium and catalyst is reported. The biodegradable and inexpensive DES provides an efficient and convenient ionic reaction medium for the thia-Michael addition with in situ generation of S-alkylisothiouronium salts in place of thiols without the urea by-product segment. This protocol offers several advantages including short reaction times, high yields, clean reactions, and inexpensive and commercially available starting materials.
Novel atom-economic reaction: Comprehensive utilization of S-alkylisothiouronium salt in the synthesis of thioethers and guanidinium salts
Gao, Pengchao,Leng, Penglin,Sun, Qi,Wang, Xin,Ge, Zemei,Li, Runtao
, p. 17150 - 17155 (2013/09/24)
A novel atom-economic three-component one-pot reaction of a primary amine, an S-alkylisothiouronium salt and a Michael receptor is reported, which affords a guanidinium salt and thioether simultaneously. The guanidine moiety is involved in catalyzing the conjugated Michael addition of the mercaptan. The reaction proceeds under ambient conditions using a non-toxic EtOH-H2O mixture as the solvent, and the two products can be very easily purified. Complete atom economy is achieved by fully utilizing the S-alkylisothiouronium salt and converting the previously wasted mercaptan by-product into the valuable thioether.
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.
Thia-Michael addition using cheap and odorless S-alkylisothiouronium salts as thiol equivalents in water
Zhao, Yan,Ge, Ze-Mei,Cheng, Tie-Ming,Li, Run-Tao
, p. 1529 - 1532 (2008/02/04)
S-Alkylisothiouronium salt has been found to be a non-toxic, odorless and simply operational alternative of thiol for the thia-Michael addition with electron-deficient olefins. The reactions were carried out under alkaline conditions in water at room temperature within 5-20 minutes to afford the expected products in good to excellent yields. Georg Thieme Verlag Stuttgart.
Asymmetric sulfoxidation catalyzed by a vanadium bromoperoxidase: Substrate requirements of the catalyst
Andersson, Malin A.,Allenmark, Stig G.
, p. 15293 - 15304 (2007/10/03)
An investigation of the catalytic effect of vanadium bromoperoxidase (VBrPO, from Corallina officinalis) on the oxidation of a series of prochiral sulfides by hydrogen peroxide, revealed that substrates having a cis- positioned carboxyl group are oxidized
Biotransformation of organic sulfides - VIII. A predictive model for sulfoxidation by Helminthosporium species NRRL 4671
Holland, Herbert L.,Brown, Frances M.,Lakshmaiah, Gingipalli,Larsen, Brett G.,Patel, Manish
, p. 683 - 697 (2007/10/03)
The fungus Helminthosporium species NRRL 4671 converts a wide range of prochiral sulfides to the corresponding chiral sulfoxides, the majority of which have (S) configuration at sulfur. The formation of a series of chiral cyclopentyl alkyl, cyclohexyl alkyl, benzyl alkyl, and methyl alkyl sulfoxides by biotransformation of the corresponding sulfides using Helminthosporium species is described. The analysis of over 90 such biotransformations has resulted in the development of a model based on restrictive-space descriptors that has been used to rationalize these reactions, and that is proposed as a predictor of the outcome of Helminthosporium-catalyzed sulfoxidations.
