85293-39-6Relevant 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.
Metal-free photocatalytic thiol-ene/thiol-yne reactions
Kaur, Sarbjeet,Zhao, Gaoyuan,Busch, Evan,Wang, Ting
supporting information, p. 1955 - 1961 (2019/02/20)
The organic photocatalyst (9-mesityl-10-methylacridinum tetrafluoroborate) in the presence of visible light is used to initiate thiol-ene and thiol-yne reactions. Thiyl radicals are generated upon quenching the photoexcited catalyst with a range of thiols
Visible-Light-Mediated Thiol-Ene Reactions through Organic Photoredox Catalysis
Zhao, Gaoyuan,Kaur, Sarbjeet,Wang, Ting
supporting information, p. 3291 - 3294 (2017/06/23)
Synthetically useful radical thiol-ene reactions can be initiated by visible-light irradiation in the presence of an organic photocatalyst, 9-mesityl-10-methylacridinum tetrafluoroborate. The key thiyl radical intermediates are generated upon quenching of
Visible light photocatalysis with benzophenone for radical thiol-ene reactions
Singh, Manjula,Yadav, Arvind K.,Yadav, Lal Dhar S.,Singh
supporting information, p. 2206 - 2208 (2017/05/16)
We report herein a simple, metal- and oxidant-free visible light promoted strategy for an anti-Markovnikov hydrothiolation of unactivated olefins using benzophenone as an inexpensive photocatalyst at room temperature. Anti-Markovnikov adducts of a wide va
Efficient dehydrative alkylation of thiols with alcohols catalyzed by alkyl halides
Yang, Yaqi,Ye, Zihang,Zhang, Xu,Zhou, Yipeng,Ma, Xiantao,Cao, Hongen,Li, Huan,Yu, Lei,Xu, Qing
supporting information, p. 9638 - 9642 (2017/11/30)
Alcohols can be efficiently converted into the useful thioethers by a transition metal- and base-free dehydrative S-alkylation reaction with thiols or disulfides by employing alkyl halides as the effective catalyst. This simple and efficient method is a green and practical way for the preparation of thioethers, as it tolerates a wide range of substrates such as aryl and alkyl thiols, as well as benzylic, allylic, secondary, tertiary, and even the less reactive aliphatic alcohols.
Efficient Generation of C–S Bonds via a By-Product-Promoted Selective Coupling of Alcohols, Organic Halides, and Thiourea
Ma, Xiantao,Yu, Lei,Su, Chenliang,Yang, Yaqi,Li, Huan,Xu, Qing
supporting information, p. 1649 - 1655 (2017/05/29)
A metal- and base-free three-component coupling of alcohols, heteroaryl halides, and thiourea has been developed for direct and selective synthesis of heteroaryl thioethers. This method can be easily scaled up to the gram scale and extended to dialkyl thioethers, heteroaryl selenides, benzothiazoles, and some antimycobacterially-active thioethers. Mechanistic studies revealed that a by-product-promoted in situ C–O activation of alcohols to more reactive alkyl halides and slow release of the thiol and alkyl halide intermediates are the key to the high selectivity and success of the reaction. (Figure presented.).
Benign and efficient preparation of thioethers by solvent-free S-alkylation of thiols with alkyl halides catalyzed by potassium fluoride on alumina
Nguyen, Kha Ngoc,Duus, Fritz,Luu, Thi Xuan Thi
, p. 349 - 360 (2016/06/01)
The preparation of thioethers by S-alkylation of various thiols with alkyl halides under solvent-free reaction conditions using potassium fluoride on alumina (KF/Al2O3) as a solid catalyst has been investigated in detail with respect to three different modes of reaction activation (ultrasound irradiation, microwave irradiation, and conventional heating) for obtaining maximum yield of the thioether. The importance of KF/Al2O3 as a particularly efficient catalyst was corroborated for all three modes of reaction activation, although the reaction time was found to be strongly dependent on the mode of activation. The yield of the thioethers was also found to depend on the amount of the solid catalyst relative to the equimolar amounts of the two reactants.
Indium-Catalyzed Reductive Sulfidation of Esters by Using Thiols: An Approach to the Diverse Synthesis of Sulfides
Miyazaki, Takahiro,Kasai, Shinsei,Ogiwara, Yohei,Sakai, Norio
, p. 1043 - 1049 (2016/03/01)
A new reductive preparation of unsymmetrical sulfides from esters and thiols in the presence of InI3 and either 1,1,3,3-tetramethyldisiloxane (TMDS) or PhSiH3 as the reductant was developed. This protocol was applied to not only benzoic acid esters that have a methoxy, methyl, chloro, bromo, iodo, or trifluoromethyl group on the aromatic ring but also aliphatic acid esters with either aromatic or aliphatic thiols. A reaction mechanism is proposed by using Hammett plot results and several control experiments. The reductive preparation of unsymmetrical sulfides from esters and thiols by using InI3 and either 1,1,3,3-tetramethyldisiloxane (TMDS) or PhSiH3 was developed. Several mechanistic studies support that the present transformation proceeds through O,S-and S,S-acetals as the reaction intermediates. TMDS = 1,1,3,3-tetramethyldisiloxane, R = aliphatic group.
One-pot Metal-free Synthesis of Benzyl Alkyl Sulfides
Lu, Xiaogang,Wang, Hongmei,Gao, Runli,Pei, Chengxin
, p. 45 - 52 (2015/10/29)
The synthesis of sulfides is important in various fields. This paper reports an efficient, odorless, and viable protocol for the base-mediated synthesis of benzyl alkyl sulfides using thiourea. The reactions were carried out under transition-metal-free co
Redox mediators in visible light photocatalysis: Photocatalytic radical thiol-ene additions
Tyson, Elizabeth L.,Niemeyer, Zachary L.,Yoon, Tehshik P.
, p. 1427 - 1436 (2014/03/21)
Synthetically useful radical thiol-ene reactions can be initiated by visible light irradiation in the presence of transition metal polypyridyl photocatalysts. The success of this method relies upon the use of p-toluidine as an essential additive. Using th
