5398-93-6Relevant articles and documents
Thiol-free chemoenzymatic synthesis of β-ketosulfides
Heredia, Adrián A.,López-Vidal, Martín G.,Kurina-Sanz, Marcela,Bisogno, Fabricio R.,Pe?é?ory, Alicia B.
, p. 378 - 387 (2019/02/20)
A preparation of β-ketosulfides avoiding the use of thiols is described. The combination of a multicomponent reaction and a lipase-catalysed hydrolysis has been developed in order to obtain high chemical diversity employing a single sulfur donor. This methodology for the selective synthesis of a set of β-ketosulfides is performed under mild conditions and can be set up in one-pot two-step and on a gram-scale.
Substituted α-Sulfur Methyl Carbanions: Effective Homologating Agents for the Chemoselective Preparation of β-Oxo Thioethers from Weinreb Amides
Senatore, Raffaele,Ielo, Laura,Urban, Ernst,Holzer, Wolfgang,Pace, Vittorio
supporting information, p. 2466 - 2470 (2018/05/03)
The proper generation of α-thiomethyllithium reagents via reductive lithiation or deprotonation followed by reaction with variously functionalized Weinreb amides represents an excellent method to access β-oxo thioethers. The procedure is adaptable to alky
Stevens rearrangement of thioethers with arynes: A facile access to multi-substituted β-keto thioethers
Xu, Xiao-Bo,Lin, Zi-Hua,Liu, Yuyin,Guo, Jian,He, Yun
supporting information, p. 2716 - 2720 (2017/04/03)
An effective method for the synthesis of multi-substituted β-keto thioethers via Stevens rearrangement of simple β-keto thioethers with arynes has been developed. In these reactions, successive C-S/C-H/C-C bonds were formed in one pot under mild and transition-metal free conditions to afford multi-substituted β-keto thioethers in moderate to good yields.
Rh/DuanPhos-Catalyzed Asymmetric Hydrogenation of β-Acetylamino Vinylsulfides: An Approach to Chiral β-Acetylamino Sulfides
Gao, Wenchao,Lv, Hui,Zhang, Xumu
supporting information, p. 2877 - 2880 (2017/06/07)
Rh/DuanPhos-catalyzed asymmetric hydrogenation of challenging β-acetylamino vinylsulfides has been developed, affording chiral β-acetylamino sulfides with high yields and excellent ee's (up to 99% ee). This novel methodology provides an efficient and concise synthetic route to chiral β-acetylamino sulfides. The potential utility of this protocol in the synthesis of Apremilast has also been disclosed.
One-pot preparation of arylethynyl sulfides and bis(arylethynyl) sulfides
Su, Qiong,Zhao, Zi-Jian,Xu, Feng,Lou, Peng-Cai,Zhang, Kai,Xie, De-Xun,Shi, Lei,Cai, Qing-Yun,Peng, Zhi-Hong,An, De-Lie
supporting information, p. 1551 - 1557 (2013/04/23)
An efficient preparation for arylethynyl sulfides 1 and bis(arylethynyl) sulfides 2 has been accomplished through a one-pot, three-step strategy that starts from arylethanonyl sulfides and bis(arylethanonyl) sulfides, respectively, without the use of various terminal arylacetylenes as substrates. When lithium hexamethyldisilazane (LHMDS), ClP(O)(OEt)2, and LHMDS were sequentially added to a tetrahydrofuran solution of different substrates [arylethanonyl sulfides or bis(arylethanonyl) sulfides], 1 or 2 were obtained in moderate to good yields. The reaction procedure involves the formation of an enol phosphate and a subsequent base-induced elimination. An efficient preparation of arylethynyl sulfides 1 and bis(arylethynyl) sulfides 2 has been accomplished by a one-pot, three-step strategy that starts from arylethanonyl sulfides and bis(arylethanonyl) sulfides, respectively, to give 1 and 2 in moderate to good yields. The reaction mechanism involves the formation of an enol phosphate that undergoes a subsequent base-induced elimination. Copyright
Palladium-catalyzed methylation of alkynyl C(sp)-H bonds with dimethyl sulfonium ylides
Liu, Yan-Yun,Yang, Xu-Heng,Huang, Xiao-Cheng,Wei, Wen-Ting,Song, Ren-Jie,Li, Jin-Heng
, p. 10421 - 10426 (2013/11/06)
A novel palladium-catalyzed methylation protocol for the synthesis of methyl-functionalized internal alkynes has been established. This methylation method is achieved through a C(sp)-C(sp3) bond formation process and represents a new synthetic application of sulfonium ylides.
An efficient and odorless synthesis of thioethers using 2-[Bis(alkylthio)methylene]-3-oxo-N-o-tolylbutanamides as thiol equivalents
Yu, Haifeng
experimental part, p. 367 - 371 (2012/04/23)
Using 2-[bis(alkylthio)methylene]-3-oxo-N-o-tolylbutanamides 1 as odorless thiol equivalents, an efficient and odorless synthesis of thioethers has been developed. Promoted by NaOH in EtOH, the cleavage of 1 commences to generate thiolate anions, and the generated thiolate anions then react with halides to give various thioethers in good yield. It is noteworthy that only a very faint odor of thiols can be perceived during both the reaction and the workup. Using 2-[bis(alkylthio)methylene]-3-oxo-N-o-tolylbutanamides as odorless thiol equivalents, an efficient and odorless synthesis of thioethers has been developed. Promoted by NaOH in EtOH, the cleavage of 2-[bis(alkylthio)methylene] -3-oxo-N-o-tolylbutanamides commences to generate thiolate anions, and the generated thiolate anions then react with halides to give various thioethers in good yield. Copyright
An efficient and practical synthesis of aryl and hetaryl α-keto esters
Raghunadh, Akula,Meruva, Suresh Babu,Kumar, Nuka Anil,Kumar, Gudla Santosh,Rao, L. Vaikunta,Syamkumar
, p. 283 - 289 (2012/03/26)
A general and highly efficient method was developed for the synthesis of -keto esters by oxidative esterification of 2,2-dibromo-1-(het)arylethanones by sequential treatment with dimethyl sulfoxide and an alkanol. The versatility of the reaction was established by synthesizing a range of -keto esters by treatment of 2,2-dibromoethanones, derived from aryl or hetaryl ketones, with di-methyl sulfoxide and a cyclic or acyclic primary or secondary alcohol. The mechanism of the reaction was established by means of a detailed study. Georg Thieme Verlag Stuttgart · New York.
Gold-catalyzed carbene transfer to alkynes: Access to 2,4-disubstituted furans
Kramer, Soren,Skrydstrup, Troels
supporting information; experimental part, p. 4681 - 4684 (2012/06/30)
Furans of gold: The first example of a gold-catalyzed intermolecular addition of carbon ylides to terminal alkynes is reported (see scheme; DCE=dichloroethane, Tf=trifluoromethanesulfonyl). Subsequent intramolecular trapping of the generated gold carbene completes a formal [3+2] cycloaddition, which represents a novel synthesis of 2,4-disubstituted furans. Copyright
Rhodium-catalyzed α-methylthiolation reaction of unactivated ketones using 1,2-diphenyl-2-methylthio-1-ethanone for the methylthio transfer reagent
Arisawa, Mieko,Toriyama, Fumihiko,Yamaguchi, Masahiko
experimental part, p. 2305 - 2312 (2011/04/22)
In the presence of catalytic amounts of RhH(PPh3)4, 1,2-bis(diphenylphosphino)ethane (dppe), and dimethyl disulfide, ketones without α-activating groups were α-methylthiolated with 1,2-diphenyl-2-methylthio-1-ethanone giving α-methylthio ketones. The reaction of unsymmetrical ketones proceeded at the more substituted carbons. The initial formation of kinetic α-methylthiolated products followed by their rearrangement to thermodynamic products was observed in the reaction of α-phenyl ketones. Aldehydes, phenylacetate, and phenylacetonitrile were also α-methylthiolated under these conditions.
