57205-13-7Relevant academic research and scientific papers
Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives
Kearney, Aoife M.,Murphy, Linda,Murphy, Chloe C.,Eccles, Kevin S.,Lawrence, Simon E.,Collins, Stuart G.,Maguire, Anita R.
, (2021/05/04)
The synthesis of a range of novel α-sulfenyl-β-chloroenones from the corresponding α-sulfenylketones, via a NCS mediated chlorination cascade, is described. The scope of the reaction has been investigated and compounds bearing alkyl- and arylthio substituents have been synthesised. In most instances, the Z α-sulfenyl-β-chloroenones were formed as the major products, while variation of the substituent at the β-carbon position led to an alteration in stereoselectivity. Stille cross-coupling with the Z α-sulfenyl-β-chloroenones led to selective formation of Z sulfenyl chalcones, while the E α-sulfenyl-β-chloroenones did not react under the same conditions. Oxidation of the Z α-sulfenyl-β-chloroenones was followed by isomerisation, leading to the E α-sulfinyl-β-chloroenones. Stille cross-coupling with the E α-sulfinyl-β-chloroenones produced the E sulfinyl chalcones. Either the E or Z sulfinyl chalcones can be obtained by altering the sequence of oxidation and Stille cross-coupling.
Synthesis of α-heterosubstituted ketones through sulfur mediated difunctionalization of internal alkynes
Zhang, Zhong,Luo, Yuzheng,Du, Hongguang,Xu, Jiaxi,Li, Pingfan
, p. 5156 - 5161 (2019/06/05)
Synthesis of α-heterosubstituted ketones was achieved through sulfur mediated difunctionalization of internal alkynes in one pot. The reaction design involves: phenyl substituted internal alkyne attacking triflic anhydride activated diphenyl sulfoxide to
Catalytic, Enantioselective Sulfenylation of Ketone-Derived Enoxysilanes
Denmark, Scott E.,Rossi, Sergio,Webster, Matthew P.,Wang, Hao
supporting information, p. 13016 - 13028 (2015/09/15)
A catalytic, enantioselective, Lewis base-catalyzed α-sulfenylation of silyl enol ethers has been developed. To avoid acidic hydrolysis of the silyl enol ether substrates, a sulfenylating agent that did not require additional Br?nsted acid activation, namely N-phenylthiosaccharin, was developed. Three classes of Lewis bases - tertiary amines, sulfides, and selenophosphoramides - were identified as active catalysts for the α-sulfenylation reaction. Among a wide variety of chiral Lewis bases in all three classes, only chiral selenophosphoramides afforded α-phenylthio ketones in generally high yield and with good enantioselectivity. The selectivity of the reaction does not depend on the size of the silyl group but is highly sensitive to the double bond geometry and the bulk of the substituents on the double bond. The most selective substrates are those containing a geminal bulky substituent on the enoxysilane. Computational analysis revealed that the enantioselectivity arises from an intriguing interplay among sterically guided approach, distortion energy, and orbital interactions.
Rhodium-catalyzed organothio exchange reaction of α-organothioketones with disulfides
Arisawa, Mieko,Toriyama, Fumihiko,Yamaguchi, Masahiko
experimental part, p. 1349 - 1352 (2010/12/24)
RhH(PPh3)4 and 1,2-bis(diphenylphosphino)ethane (dppe) catalyzed the organothio exchange reaction of α-organothioketones and organic disulfides. The reaction was affected by the structure of the substrate: α-phenylthio and α-alkylthio aryl ketones reacted effectively with diaryl and dialkyl disulfides; α-phenylthio dialkyl ketones reacted with diaryl disulfides but not with dialkyl disulfides; diaryl disulfides with electron-donating p-substituents were more reactive than those with electron-withdrawing p-substituents.
Electrophilic Addition of 4'-Nitrobenzenesulphenanilide to Alkynes in Acetic Acid. A Synthesis of β-Acetoxyvinyl Sulphides
Benati, Luisa,Casarini, Daniele,Montevecchi, Pier Carlo,Spagnolo, Piero
, p. 1113 - 1116 (2007/10/02)
4'-Nitrobenzenesulphenanilide reacts at room temperature with simple alkyl- and aryl-alkynes in acetic acid in the presence of boron trifluoride-diethyl ether to afford products of acetoxysulphenylation in moderate to good yields.The addition products are
A CONVENIENT SYNTHESIS OF Β-KETO PHENYL SULPHIDES FROM ALKYNES.
Benati, L.,Montevecchi, P.C.,Spagnolo, P.
, p. 2381 - 2384 (2007/10/02)
β-Keto sulphides can be conveniently prepared by BF3-promoted reaction of 4'-nitrobenzenesulphenanilide in acetonitrile or acetic acid and subsequent hydrolysis of the resulting β-acetamidino- or β-acetoxy-vinyl phenyl sulphides.
Asymmetric Sulfenylation of Tin(II) Enolates of Ketones and 3-Acyl-2-oxazolidones. Application to the Synthesis of Optically Active Epoxides
Yura, Takeshi,Iwasawa, Nobuharu,Clark, Richard,Mukaiyama, Teruaki
, p. 1809 - 1812 (2007/10/02)
In the presence of chiral diamines, the reaction between tin(II) enolates of ketones or 3-acyl-2-oxazolidones and thiosulfonates proceeds smoothly to give the corresponding β-keto sulfides with high enetioselectivity.Further, optically active epoxides are prepared from these β-keto sulfides.
Oxidative S-Dealkylation Reaction of Sulfide Catalyzed by Co(II)(bzacen)
Watanabe, Yoshihito,Numata, Tatsuo,Oae, Shigeru
, p. 1915 - 1920 (2007/10/02)
In the oxygenation reaction of alkyl sulfides with Co(II)(bzacen)-O2 system, oxidative S-C bond cleavage (S-dealkylation) was found to take place exclusively.The reactivity of S-dealkylation reaction was dependent markedly on both acidity of α-methylene and steric hindrance of alkyl sulfide.The peroxo-Co(III) species is presumed to be the intermediate in this S-dealkylation reaction.
