76216-50-7Relevant academic research and scientific papers
Zinc-catalyzed regioselective addition of alkyl thiols to alkenes via anion or radical reactions
Taniguchi, Nobukazu
, p. 125 - 137 (2021/03/17)
Zn-catalyzed reactions of alkenes with alkyl thiols could afford alkyl sulfides regioselectively. When the ZnI2- catalyzed hydrothiolation of alkenes was achieved using alkyl thiols at 100 °C, Markovnikov-type alkyl sulfides were obtained in excellent yields without the formation of linear products. To the contrary, Zn(OAc)2- catalyzed reaction gave rise only to anti-Markovnikov-type products regioselectively. The reaction proceeded via a radical process.
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
supporting information, 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.
A novel approach to the practical synthesis of sulfides: An InBr 3-Et3SiH catalytic system promoted the direct reductive sulfidation of acetais with disulfides
Sakai, Norio,Moritaka, Kohei,Konakahara, Takeo
experimental part, p. 4123 - 4127 (2009/12/09)
We have demonstrated a facile and direct synthesis of sulfide derivatives using acetais and ketals, derived, from aromatic/ conjugated, aldehydes and aromatic ketones, with disulfides and the InBr3-Et3SiH reducing system., We also succeeded in developing an unprecedented one-pot preparation of an aliphatic sulfide from a disulfide and an aliphatic acetal. (Wiley-VCH Verlag GmbH & Co. KGaA.
A NEW SYNTHESIS OF SULFIDES FROM THIOLS AND ALDEHYDES OR KETONES WITH PYRIDINE-BORANE IN TRIFLUOROACETIC ACID
Kikugawa, Yasuo
, p. 1157 - 1158 (2007/10/02)
A mixture of thiols and aldehydes or ketones was converted into sulfides with pyridine-borane in trifluoroacetic acid.
