112445-70-2Relevant academic research and scientific papers
Asymmetric Catalytic [2,3] Stevens and Sommelet–Hauser Rearrangements of α-Diazo Pyrazoleamides with Sulfides
Lin, Xiaobin,Yang, Wei,Yang, Wenkun,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 13492 - 13498 (2019/08/28)
Catalytic enantioselective [2,3] Stevens and Sommelet–Hauser rearrangements of α-diazo pyrazoleamides with sulfides were achieved by utilizing chiral N,N′-dioxide/nickel(II) complex catalysts. These rearrangements proceeded well under mild reac
Gold-Catalyzed Oxidation of Thioalkynes to Form Phenylthio Ketene Derivatives via a Noncarbene Route
Sharma, Pankaj,Singh, Rahulkumar Rajmani,Giri, Sovan Sundar,Chen, Liang-Yu,Cheng, Mu-Jeng,Liu, Rai-Shung
, p. 5475 - 5479 (2019/08/01)
Gold-catalyzed oxidations of thioalkynes with 8-methylquinoline oxides afford 2-phenylthioketenes that can be trapped efficiently with alcohols. The synthetic utility is manifested by terminal and internal thioalkynes over a wide scope, bearing esters, ke
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.
Fluorination of α-phenylsulfanyl esters using difluoroiodotoluene
Motherwell, William B.,Greaney, Michael F.,Tocher, Derek A.
, p. 2809 - 2815 (2007/10/03)
Treatment of α-phenylsulfanyl esters 11-14 with one equivalent of difluoroiodotoluene 3a produced the α-fluoro sulfides 17-20 in good overall yield through a Fluoro-Pummerer reaction. A second equivalent of reagent produced α,α-difluoro sulfides and a third led to α,α-difluoro sulfoxides. An identical pattern of reactivity was observed with the α-phenylsulfanyl lactone 26. This sequential fluorination-oxidation behaviour was exploited in the one-pot synthesis of 3-fluoro-2(5H)-furanone 33 starting from α-phenylsulfanylbutyrolactone 32.
