7133-37-1Relevant academic research and scientific papers
Copper-Catalyzed direct thioetherification of Alkyl Halides with S-Alkyl Butanethioate as Thiol transfer reagent
Li, Yahui,Tian, Qingqiang,Wang, Lili
, (2021/08/30)
A new and convenient copper-catalyzed synthesis of alkyl sulfides has been accomplished using S-alkyl butanethioate as a thiol source. This catalytic protocol displayed a good functional groups tolerance and high efficiency. Both secondary and primary alkyl iodides can be used in this procedure. In addition, this method features operational simplicity and a wide substrate range, providing a complementary method for alkyl sulfide synthesis without requiring toxic thiols and noble metals.
Transition metal-free formal hydro/deuteromethylthiolation of unactivated alkenes
Chen, Shuangyang,Wang, Jia,Xie, Lan-Gui
supporting information, p. 4037 - 4042 (2021/05/19)
Methylthioether is involved in the methylthiotransfer process in organisms, and therefore its functionality is of paramount importance to living organisms. Several methods for the installation of the methylthio group in small molecules have been reported previously; however, procedures starting from unactivated alkenes are rare. Herein, we report a formal hydro/deuteromethylthiolation of alkenes by using dimethyl(methylthio)sulfonium trifluoromethanesulfonate as the stimulator and sodium borohydride/deuteride as the hydrogen/deuterium source. The process represents a mild, transition metal-free and methanethiol-free route towards the synthesis of methylthioethers from unactivated alkenes. This journal is
Ex Situ Formation of Methanethiol: Application in the Gold(I)-Promoted Anti-Markovnikov Hydrothiolation of Olefins
Kristensen, Steffan K.,Laursen, Simon L. R.,Taarning, Esben,Skrydstrup, Troels
supporting information, p. 13887 - 13891 (2018/10/02)
A protocol for the Au-promoted anti-Markovnikov hydrothiolation of olefins using ex situ generated methanethiol is reported. The use of S-methylisothiourea hemisulfate salt as a solid precursor for methanethiol generation ensures a safe and reliable deliverance of a stoichiometric amount of this thiol. The procedure was shown to work for a broad range of olefins providing the corresponding hydrothiolated adduct in good to excellent yields. Mechanistic evaluations suggest that thiyl radicals are generated and that gold acts as an efficient but stable radical initiator.
Enantioselective copper catalysed intramolecular C-H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent
Shiely, Amy E.,Slattery, Catherine N.,Ford, Alan,Eccles, Kevin S.,Lawrence, Simon E.,Maguire, Anita R.
supporting information, p. 2609 - 2628 (2017/04/01)
Enantioselectivities in C-H insertion reactions, employing the copper-bis(oxazoline)-NaBARF catalyst system, leading to cyclopentanones are highest with sulfonyl substituents on the carbene carbon, and furthermore, the impact is enhanced by increased steric demand on the sulfonyl substituent (up to 91%ee). Enantioselective intramolecular C-H insertion reactions of α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones are reported for the first time.
B(C6F5)3-Catalyzed Deoxygenation of Sulfoxides and Amine N-Oxides with Hydrosilanes
Ding, Fangwei,Jiang, Yanqiu,Gan, Shaoyan,Bao, Robert Li-Yuan,Lin, Kaifeng,Shi, Lei
, p. 3427 - 3430 (2017/07/04)
An efficient strategy for the deoxygenation of sulfoxides and amine N-oxides by using B(C6F5)3 and hydrosilanes was developed. This method provided the corresponding aromatic and aliphatic products in good to high yields and showed good functional-group tolerance under mild conditions.
Sulfoxide-to-sulfilimine conversions: Use of modified Burgess-type reagents
Hendriks, Christine M. M.,Lamers, Philip,Engel, Julien,Bolm, Carsten
supporting information, p. 3363 - 3368 (2013/12/04)
Sulfoxides can directly be converted into N-cyanosulfilimines using a new Burgess-type reagent. By applying this strategy with a related reagent variant, synthetically valuable NH-sulfoximines have been prepared from sulfoxides via N-protected sulfilimines. The practical three-step reaction sequence is generally high yielding and applicable to a wide range of substrates. The sulfoxide-to-sulfilimine conversion can also be performed under solvent-reduced conditions in a ball mill. Copyright
Enantioselective nitrene transfer to sulfides catalyzed by a chiral iron complex
Wang, Jun,Frings, Marcus,Bolm, Carsten
supporting information, p. 8661 - 8665 (2013/09/12)
Iron works: Enantioselective nitrene transfer to sulfide was accomplished by a chiral iron(III)/PyBOX catalyst (see scheme). Various sulfimides were thus obtained in high enantioselectivities and yields. Applications of this protocol to the syntheses of enantioenriched sulfoximines and an epoxide were also demonstrated. Copyright
Synthesis of organic sulfides using Ce-exchanged NaY catalyst
Reddy, T. Indrasena,Varma, Rajender S.
, p. 621 - 622 (2007/10/03)
Synthesis of organic sulfides from thiols and alkyl halides is achieved using Ce-exchanged zeolite catalyst, Ce(72percent)NaY.
Reactions of the Radical with Unsaturated Cycloalkanes: Abstraction, Addition, and Rearrangement
Lunazzi, Lodovico,Placucci, Giuseppe,Grossi, Loris
, p. 703 - 707 (2007/10/02)
The methylthiyl radical (MeS*) generated by photolysis of dimethyl disulphide (MeSSMe) is shown to give three types of reactions with cyclic molecules containing carbon-carbon double bonds.E.s.r. spectra corresponding to radicals formed by addition of MeS*, by hydrogen abstraction, and by rearrangement (possibly involving 1,4-hydrogen shift between SMe and the radical centre) have been detected.In the case of cyclopentene, all three types of radicals were observed.In the case of cyclohexene, only radicals due to abstraction and rearrangement were detected.With methylenecycloalkanes there was no evidence for hydrogen abstraction but radicals from addition and rearrangement were identified.
Metalation of 1,3-Dithiolanes. Mercaptan Synthesis and Carbonyl Transposition
Wilson, Stephen R.,Georgiadis, Gregory M.,Khatri, Hiralal N.,Bartmess, John E.
, p. 3577 - 3583 (2007/10/02)
The reaction of 1,3-dithiolanes with n-butyllithium results in fragmentation to the corresponding thiocarbonyl compound followed by furhter reaction with n-butyllithium.All four types of thiocarbonyl reactions are observed: reduction, S-addition, C-addition, double addition.Synthetic applications of this reaction for the synthesis of secondary mercaptans and 1,2-carbonyl transposition (23 -> 24a-c) are described.
