34005-03-3Relevant articles and documents
Transition-Metal-Free and Base-Promoted Carbon-Heteroatom Bond Formation via C-N Cleavage of Benzyl Ammonium Salts
Liu, Long,Tang, Yuanyuan,Wang, Kunyu,Huang, Tianzeng,Chen, Tieqiao
, p. 4159 - 4170 (2021/03/09)
A facile and general method for constructing carbon-heteroatom (C-P, C-O, C-S, and C-N) bonds via C-N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated. The scale-up reaction and one-pot synthesis were also successfully performed.
Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides
Luo, Jie,Rauch, Michael,Avram, Liat,Ben-David, Yehoshoa,Milstein, David
supporting information, p. 21628 - 21633 (2021/01/11)
Direct hydrogenation of thioesters with H2 provides a facile and waste-free method to access alcohols and thiols. However, no report of this reaction is documented, possibly because of the incompatibility of the generated thiol with typical hydrogenation catalysts. Here, we report an efficient and selective hydrogenation of thioesters. The reaction is catalyzed by an acridine-based ruthenium complex without additives. Various thioesters were fully hydrogenated to the corresponding alcohols and thiols with excellent tolerance for amide, ester, and carboxylic acid groups. Thiocarbamates and thioamides also undergo hydrogenation under similar conditions, substantially extending the application of hydrogenation of organosulfur compounds.
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
1,2-dibromotetrachloroethane: An ozone-friendly reagent for the in situ Ramberga-Baecklund rearrangement and its use in the formal synthesis of E-resveratrol
Soiderman, Stefan C.,Schwan, Adrian L.
, p. 10978 - 10984 (2013/02/23)
Dibromotetrachloroethane (C2Br2Cl4) is demonstrated as a halogenating reagent for the one-pot conversion of sulfones to alkenes by way of the Ramberga-Baecklund rearrangement. Dibromotetrachloroethane successfully replaces known ozone depleting agents CCl4, CBr2F2 and C2Br 2F4. A formal synthesis of E-resveratrol is demonstrated using C2Br2Cl4.
Synthesis of sulfides under solvent- and catalyst-free conditions
Movassagh, Barahman,Soleiman-Beigi, Mohammad
experimental part, p. 409 - 411 (2010/05/01)
A simple, highly efficient, and green protocol has been developed for preparation of sulfides from alkyl or aryl thiols and benzyl-, allyl-, t-butyl, and adamantyl halides under solvent- and catalyst-free conditions.
CeCl3/Sm induced reductive cleavage of the S-S bond in disulfide: A novel method for the synthesis of β-thioesters, thiol-esters and alkylphenyl sulfides
Li, Xue,Zhang, Songlin,Zhang, Yongmin
, p. 1527 - 1529 (2007/10/03)
Disulfide has been reduced by cerium trichloride and samarium in tetrahydrofuran to produce samarium thiolates. The "living" species reacts smoothly with α,β-unsaturated esters(nitriles) to afford β-thioesters(nitrile) under mild and neutral conditions. The new thiolate anion also reacts with acyl halides, anhydrides and alkyl or benzyl halides to give thioesters and sulfides, respectively.
Preparation of unsymmetrical sulfides using modified zeolite catalysts
Esakkidurai,Vijaikumar,Madhavan,Pitchumani
, p. 3142 - 3144 (2007/10/03)
Reaction between benzyl chlorides and thiols is catalysed efficiently by novel modified mildly basic zeolites, prepared by introducing 3-aminopropyltriethoxysilane and tetra(ethyleneglycol)dimethyl ether into the cages of NaY zeolites and high yields of the corresponding sulfides are obtained.
Reductive Cleavage of the S-Si Bond in Arylsulfanyltrimethylsilanes: A Novel Method for the Synthesis of Unsymmetrical Sulfides
Zhang, Songtin,Zhang, Yongmin M.
, p. 48 - 49 (2007/10/03)
Arylsulfanyltrimethylsilanes are reduced by samarium diiodide to yield samarium arylthiolates which react with alkyl halides to give unsymmetrical sulfides.
Synthesis of organic sulfides from thiols using montmorillonite-3-aminopropyltriethoxysilane as a new catalyst
Kannan,Pitchumani,Rajagopal,Srinivasan
, p. 369 - 370 (2007/10/03)
A new basic clay, synthesised by introducing 3-aminopropyltriethoxysilane into montmorillonite, catalyses the reaction between benzyl chloride and thiols to afford high yields of the corresponding sulfides. ? To whom correspondence should be addressed.
Free-Radical Addition of Alkanethiols to Alkynes. Rearrangements of the Intermediate β-Thiovinyl Radicals
Benati, Luisa,Capella, Laura,Montevecchi, Pier Carlo,Spagnolo Piero
, p. 2818 - 2823 (2007/10/02)
A variety of 2-mercapto-substituted vinyl radicals have been produced through the free-radical reaction of alkanethiols (including phenethyl, allyl, and benzyl mercaptans) with monosubstituted acetylenes in benzene at 90 deg C.The 2-(benzylthio)vinyl radi