46188-84-5Relevant academic research and scientific papers
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.
supporting information, 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
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
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.
Reaction of ammonium ylides with alkyl thiocyanates in aqueous and non-aqueous media
Kianmehr, Ebrahim,Mirza Agha, Mansoureh,Estiri, Hamid
experimental part, p. 409 - 411 (2011/07/30)
Reaction of ammonium ylides with alkyl thiocyanates in aqueous and non-aqueous media is described. The reaction leads to alkyl thio-substituted acetophenones via addition of ammonium ylides to alkyl thiocyanates in organic solvents or in situ generated thiolate anions in aqueous media.
α, α-gem-difluorination of α-(alkylthio)acetophenone derivatives with N-Fluoropyridinium salts
Takeda, Sunao,Kaneko, Yasushi,Eto, Hiromichi,Tokizawa, Minoru,Sato, Susumu,Yoshida, Kouiti,Namiki, Setsuo,Ogawa, Masaki
, p. 1097 - 1100 (2007/10/03)
The α, α-gem-difluorination of 2',4'-difluoro- α(methylthio)acetophenone (1a) with N-fluoropyridinium salts gave 2',4',α-tetrafluoro-α-(methylthio)acetophenone (3a). This reaction was accelerated by the addition of zinc chloride, zinc bromide or anhydrous iron(III) chloride, and higher yields than the reaction without additives were obtained. The gem- difluorination reaction using FP-T300 in the presence of zinc bromide was applicable to other α-(alkylthio)acetophenone derivatives (1).
The Electrolytic Reduction of p-Substituted α-(Methylsulfinyl)-α-(methylthio)acetophenones in Acetonitrile
Kunugi, Akira,Takahashi, Norimasa,Abe, Kyo,Hirai, Taketsugu
, p. 2055 - 2057 (2007/10/02)
p-Substituted α-(methylsulfinyl)-α-(methylthio)-acetophenones (1) exhibit on polarographic reduction, three wavwes.The two last waves corespond to the reductions of p-substituted α-(methylthio)acetophenones (2) and p-substituted acetophenones respectively
A CONVENIENT GENERAL ACCESS TO α-SULFENYLATED ACETOPHENONES AND ALKANONES
Ishibashi, Hiroyuki,Takamuro, Iwao,Mizukami, Yo-ichi,Irie, Maki,Ikeda, Masazumi
, p. 443 - 452 (2007/10/02)
Friedel-Crafts acylation of arenes with methylthio- (1) or phenylthio-acetyl chloride (2) provides ready access to α-methylthio- or α-phenylthio-substituted acetophenones.The acyl chlorides 1 and 2 reacted also with organoaluminium reagents to give α-sulfenylated alkanones.
