75954-35-7Relevant academic research and scientific papers
Transition-metal-free decarboxylative thiolation of stable aliphatic carboxylates
Xing, Wei-Long,Liu, De-Guang,Fu, Ming-Chen
, p. 4593 - 4597 (2021/02/03)
A transition-metal-free decarboxylative thiolation protocol is reported in which primary, secondary, tertiary (hetero)aryl acetates and α-CN substituted acetates undergo the decarboxylative thiolation smoothly, to deliver a variety of functionalized aryl alkyl sulfides in moderate to excellent yields. Aryl diselenides are also amenable substrates for construction of C-Se bonds under the simple and mild reaction conditions. Moreover, the protocol is successfully applied to the late-stage modification of pharmaceutical carboxylates with satisfactory chemoselectivity and functional-group compatibility. This journal is
Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides
Li, Fuhai,Wang, Dan,Chen, Hongyi,He, Ze,Zhou, Lihong,Zeng, Qingle
, p. 13029 - 13032 (2020/11/07)
A new protocol was developed to synthesize (enantioenriched) thioethers and selenoethers from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These syntheses were promoted by the presence of weak base and did not require the use of any transition metal, and resulted in the target products with good to excellent yields (72-94%). Using quaternary ammonium salts synthesized from enantiomerically enriched amines led to highly enantiopure benzylic thioethers and selenoethers (94-99% ee) with configurations reversed from those of their enantioenriched quaternary ammonium salts. This journal is
Photochemical, Metal-Free Sigmatropic Rearrangement Reactions of Sulfur Ylides
Yang, Zhen,Guo, Yujing,Koenigs, Rene M.
supporting information, p. 6703 - 6706 (2019/05/10)
Sigmatropic rearrangement reactions constitute one of the most fundamental reactions of carbenes. While state-of-the-art synthetic methods require the use of expensive precious metal catalysts, the application of visible light for the photolysis of α-aryldiazoacetates is much less investigated and provides an operationally simple entry to carbenes under mild reaction conditions. Herein, we report on blue-light induced sigmatropic rearrangement reactions of sulfur compounds with α-aryldiazoacetates. This process, depending on the substitution pattern of the sulfide, opens up formal insertion reactions of carbenes into S?N, S?C, or C?H bonds.
Alkyl Sulfides as Promising Sulfur Sources: Metal-Free Synthesis of Aryl Alkyl Sulfides and Dialkyl Sulfides by Transalkylation of Simple Sulfides with Alkyl Halides
Liu, Ting,Qiu, Renhua,Zhu, Longzhi,Yin, Shuang-Feng,Au, Chak-Tong,Kambe, Nobuaki
supporting information, p. 3833 - 3837 (2018/12/05)
A site-selective metal-free dealkylative approach to synthesize aryl alkyl and symmetrical dialkyl sulfides has been developed. This procedure is convenient and has wide functional group tolerance giving rise to sulfides carrying various alkyl chains from simple alkyl sulfides and alkyl halides in good to excellent yields. This transalkylation proceeds by an ionic mechanism via sulfonium intermediates and it was proposed that dimethylacetamide (DMAC) may participate in part to promote the reaction.
Nano cobalt ferrite catalyzed coupling reaction of nitroarene and alkyl halide: An odorless and ligand-free rout to unsymmetrical thioether synthesis
Moghaddam, Firouz Matloubi,Pourkaveh, Raheleh
, p. 33 - 37 (2017/02/23)
This study describes an odorless protocol for the synthesis of unsymmetrical sulfides via cobalt ferrite (CoFe2O4) catalyzed cross-coupling reaction of nitroarenes with alkyl halides in the presence of thiourea as sulfur source under
Sulfide synthesis through copper-catalyzed C-S bond formation under biomolecule-compatible conditions
Zhang, Yonghong,Li, Yiming,Zhang, Xiaomei,Jiang, Xuefeng
, p. 941 - 944 (2015/01/09)
We report here an efficient and mild method for constructing C-S bonds. The reactions were carried out with Na2S2O3 as a sulfurating reagent, CuSO4 as a catalyst, and water as solvent without any surfactant. The products were achieved in moderate to excellent yields at room temperature under air. Notably, this reaction is compatible with various biomolecules including amino acids, oligosaccharides, nucleosides, proteins, and cell lysates. This journal is
The reaction of grignard reagents with bunte salts: A thiol-free synthesis of sulfides
Reeves, Jonathan T.,Camara, Kaddy,Han, Zhengxu S.,Xu, Yibo,Lee, Heewon,Busacca, Carl A.,Senanayake, Chris H.
supporting information, p. 1196 - 1199 (2014/03/21)
S-Alkyl, S-aryl, and S-vinyl thiosulfate sodium salts (Bunte salts) react with Grignard reagents to give sulfides in good yields. The S-alkyl Bunte salts are prepared from odorless sodium thiosulfate by an SN2 reaction with alkyl halides. A Cu-
Camphorquinone: A new and efficient oxidant for the preparation of 2-thio-substituted benzothiazoles from alcohols by oxidation-reduction condensation
Pluempanupat, Wanchai,Temyarasilp, Parinthorn,Widhalm, Michael,Chavasiri, Warinthorn
, p. 418 - 430 (2014/06/10)
A convenient one-pot procedure for the preparation of various 2-thio-substituted benzothiazoles from alcohols and benzothiazole-2-thiol utilizing camphorquinone-mediated oxidation-reduction condensation is disclosed. The condensation between benzothiazole-2-thiol and alkyl diphenylphosphinites, generated in situ from alcohols and chlorodiphenylphosphine, proceeded smoothly in the presence of camphorquinone to furnish the corresponding benzothiazoles in good to moderate yields.
Mild and efficient deoxygenation of sulfoxides to sulfides with triflic anhydride/potassium iodide reagent system
Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Karimi, Ahmad
experimental part, p. 2543 - 2546 (2009/04/04)
It was found that the combination of triflic anhydride/potassium iodide was an effective promoter for the deoxygenation of sulfoxides and gave the corresponding sulfides in excellent yield in acetonitrile at room temperature. It is worth mentioning that this reagent system is chemoselective and tolerates various functional groups, such as alkene, ketone, ester, aldehyde, acid, and oxime. Georg Thieme Verlag Stuttgart.
A novel method for the deoxygenation of sulfoxides with the PPh 3/Br2/CuBr system
Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Khedri, Mohammad
, p. 1324 - 1325 (2008/03/18)
It was found that the combination of PPh3/Br2/CuBr was an effective promoter for the deoxygenation of sulfoxides and gave the corresponding sulfides in excellent yield in acetonitrile under refluxing conditions. It is worth mentioning that this reagent system is chemoselective, tolerating various functional groups such as carbon-carbon double bond and ketone. Copyright
