97839-36-6Relevant academic research and scientific papers
Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters
Cao, Han,Liu, Xuejing,Bie, Fusheng,Shi, Yijun,Han, Ying,Yan, Peng,Szostak, Michal,Liu, Chengwei
, p. 10829 - 10837 (2021/07/28)
Decarbonylative synthesis of thioethers from thioesters proceeds in the presence of a catalytic amount of [Rh(cod)Cl]2 (2 mol %). The protocol represents the first Rh-catalyzed decarbonylative thioetherification of thioesters to yield valuable thioethers. Notable features include the absence of phosphine ligands, inorganic bases, and other additives and excellent group tolerance to aryl chlorides and bromides that are problematic using other metals to promote decarbonylation. Gram scale synthesis, late-stage pharmaceutical derivatization, and orthogonal site-selective cross-couplings by C-S/C-Br cleavage are reported.
Fukuyama Cross-Coupling Approach to Isoprekinamycin: Discovery of the Highly Active and Bench-Stable Palladium Precatalyst POxAP
Tang, Shuang-Qi,Bricard, Jacques,Schmitt, Martine,Bihel, Frédéric
supporting information, p. 844 - 848 (2019/01/30)
An efficient and user-friendly palladium(II) precatalyst, POxAP (post-oxidative-addition precatalyst), was identified for use in Fukuyama cross-coupling reactions. Suitable for storage under air, the POxAP precatalyst allowed reaction between thioesters and organozinc reagents with turnover numbers of ～90000. A series of 23 ketones were obtained with yields ranging from 53 to 99%. As proof of efficacy, an alternative approach was developed for the synthesis of a key precursor of the natural product isoprekinamycin.
Syntheses of thiol and selenol esters by oxidative coupling reaction of aldehydes with RYYR (Y = S, Se) under metal-free conditions
He, Chunhuan,Qian, Xuewei,Sun, Peipei
supporting information, p. 6072 - 6075 (2014/08/05)
Thiol and selenol esters were synthesized by a direct oxidative coupling reaction of aldehydes with disulfides or diselenides in ethyl acetate under metal-free conditions. Among the oxidants examined, tert-butyl peroxide (TBP) was shown to give the best results. For the substrates with both electron-donating and electron-withdrawing substituents, the reaction proceeded smoothly and gave moderate to good yields. Compared with the previous method, the present route is very simple, atom-economical and environmentally friendly. This journal is the Partner Organisations 2014.
Polymer supported Pd catalyzed thioester synthesis via carbonylation of aryl halides under phosphine free conditions
Islam, Sk Manirul,Molla, Rostam Ali,Roy, Anupam Singha,Ghosh, Kajari
, p. 26181 - 26192 (2014/07/08)
A new polymer supported phosphine free Pd(ii) complex has been synthesized and characterized. The catalytic performance of the complex has been tested for the carbonylation of aryl halides into aryl thioesters under mild reaction conditions. Thioesters were obtained in excellent yields from various aryl iodides and thiols in the presence of carbon monoxide and polymer supported palladium catalyst. The effects of solvent, base, reaction time and catalyst amount for the thioester synthesis were reported. This catalyst showed excellent catalytic activity and recyclability. The polymer supported Pd(ii) catalyst could be easily recovered by filtration and reused more than five times without appreciable loss of its initial activity.
Tetraethylammonium bromide-catalyzed oxidative thioesterification of aldehydes and alcohols
Zhu, Xuebin,Shi, Yan,Mao, Haibin,Cheng, Yixiang,Zhu, Chengjian
supporting information, p. 3558 - 3562 (2014/01/06)
A metal-free, tetraethylammonium bromide-catalyzed oxidative coupling of aldehydes or alcohols with thiophenols or disulfides has been developed. This protocol affords an efficient and inexpensive approach to the synthesis of a wide range of thioesters in high yields. Copyright
Pd-catalyzed thiocarbonylation with stoichiometric carbon monoxide: Scope and applications
Burhardt, Mia N.,Taaning, Rolf H.,Skrydstrup, Troels
supporting information, p. 948 - 951 (2013/03/28)
A general protocol for the Pd-catalyzed thiocarbonylation of aryl iodides with stoichiometric carbon monoxide has been established employing a catalytic system composed of Pd(OAc)2 and DPEphos with low catalyst loading (1 mol %). Both electron-rich and -deficient aryl iodides proved effective for these couplings with aryl and alkyl thiols. The choice of the metal ligands and the solvent system was crucial for the efficiency and chemoselectivity of these transformations.
Reductive cleavage of the sulfur-sulfur bond by the samarium/Cp 2TiCI2 used for the synthesis of S-phenyl thiolesters
Jia, Xueshun,Zhang, Yongmin
, p. 540 - 541 (2007/10/03)
A mild method is reported for the reductive cleavage of the sulfur-sulfur bond by the samarium/ Cp2TICI2 system to give a phenylthiolate anion species which reacts with acyl chlorides to give the corresponding S-phenyl thiolesters in
Reductive cleavage of S-S bond in diphenyl disulfide by samarium diiodide: A novel method for the synthesis of thiolesters
Jia,Zhang,Zhou
, p. 387 - 392 (2007/10/02)
Diphenyl disulfide is reduced by samarium diiodide to yield samarium phenylthiolate. This new thiolate anion species mildly reacts with acyl chlorides to give thiolesters in good yields.
A Novel Method of Synthesis of 2-Methylthio-1,3-oxazoles
Alvarez-Ibarra, Carlos,Mendoza, Magnolia,Orellana, Guillermo,Quiroga, Maria L.
, p. 560 - 562 (2007/10/02)
A one-pot synthesis of 2-methylthio-1,3-oxazoles by a cyclocondensation reaction between dimethyl N-(ethoxycarbonylmethyl)iminodithiocarbonate and S-phenyl alkanethioates and thiobenzoates is described.The new procedure offers several advantages: easy access of the reagents, high selectivity, and facile introduction of different substitutions in the heterocyclic ring.
