99967-65-4Relevant academic research and scientific papers
Microwave-Assisted Pd-Catalyzed Desulfitative C-S Coupling of Arylsulfinate Metal Salts and Alkanethiols
Li, Junchen,Bi, Xiaojing,Wang, Hongmei,Xiao, Junhua
, p. 1873 - 1881 (2014)
This paper reports a palladium-catalyzed C-S coupling of arylsulfinate metal salts and alkanethiols via liberation of sulfur dioxide. The use of PdCl2 as the catalyst in combination with AgNO3 as the oxidant under microwave irradiation results in the synthetically and biologically important aryl alkyl sulfides. A variety of arylsulfinate metal salts, such as sodium, potassium, lithium, silver, zinc, and copper salts, are tolerated well in this reaction.
Direct access to α-sulfenylated amides/esters: Via sequential oxidative sulfenylation and C-C bond cleavage of 3-oxobutyric amides/esters
Jiang, Yi,Deng, Jie-Dan,Wang, Hui-Hong,Zou, Jiao-Xia,Wang, Yong-Qiang,Chen, Jin-Hong,Zhu, Long-Qing,Zhang, Hong-Hua,Peng, Xue,Wang, Zhen
supporting information, p. 802 - 805 (2018/02/06)
An efficient, environmentally benign and unprecedented synthesis of various α-sulfenylated amides/esters has been developed under oxygen atmosphere. The reaction shows good functional group tolerance and excellent chemo/regioselectivity. All the desired products were obtained in moderate to excellent yields, even on the gram scale. Practically, the related α-thiol Weinreb amide can be readily transferred to a series of prospective compounds, and selenium atom can be introduced to the α-sites of the amides in high yields.
Copper-Catalyzed Synthesis of α-Thioaryl Carbonyl Compounds Through S-S and C-C Bond Cleavage
Zou, Liang-Hua,Priebbenow, Daniel L.,Wang, Long,Mottweiler, Jakob,Bolm, Carsten
supporting information, p. 2558 - 2563 (2013/10/21)
A method to access α-thioaryl ketones and α-thioaryl esters employing copper acetate (hydrate) as catalyst and readily accessible diaryl disulfides and β-diketones (or β-keto esters) has been developed. Both alkyl- and aryl-substituted carbonyl compounds can be prepared. Copyright
Origin of the Stereoselectivity in (Ethoxycarbonyl)-, Cyano-, and Phenyl-Substituted (Arylsulfinyl)methyl Radicals
Renaud, Philippe,Bourquard, Thierry,Carrupt, Pierre-Alain,Gerster, Michèle
, p. 1048 - 1063 (2007/10/03)
An explanation for the very high diastereoselectivity observed for the reactions of carbonyl-substituted (arylsulfmyl)methyl radicals is presented, based on experimental results and semiempirical calculations. The influence of dipole-dipole interactions, allylic 1,3-strain(A1,3 strain), allylic 1,2-strain (A1,3 strain), and coulombic interactions is discussed based on stereoselectivities observed with (alkoxycarbonyl)-, cyano-, and aryl-substituted (arylsulfinyl)methyl radicals. In the second part, the effect of solvents and Lewis acids on the stereoselectivity of. reactions of (arylsulfmyl)- and (alkylsulfinyl)benzyl radicals has been examined.
Ligand exchange reaction of sulfoxides in organic synthesis: A novel method for generation of magnesium enolates and its application to synthesis of α-halocarboxylic acid derivatives and α-haloaldehydes
Satoh,Kitoh,Onda,Takano,Yamakawa
, p. 4957 - 4972 (2007/10/02)
A new method for synthesis of α-halo(Cl, F)carboxylic acid derivatives and α-haloaldehydes is described. α-Halo-α-sulfinyl carboxylic acid, esters, and α-halo-α-sulfinyl aldehydes were easily prepared from aryl 1-haloalkyl sulfoxides and alkyl chloroformate and ethyl formate, respectively, in good yields. α-Chloro-α-sulfinyl amides were synthesized from (p-tolylthio)acetic acid. Ligand exchange reaction of the sulfinyl group of these acids, esters, amides, and aldehydes with ethylmagnesium bromide gave the magnesium enolates, which were treated with water to give α-halocarboxylic acid derivatives and α-chloroaldehydes in good yields. The magnesium enolates derived from the α-chloro-α-sulfinyl acid derivatives were trapped with carbonyl compounds to afford the adducts, which were transformed to α,β-epoxy carboxylic acid derivatives. Thermal elimination of the sulfinyl group in the α-halo-α-sulfinyl acid derivatives and the α-halo-sulfinyl aldehydes gave α-halo-α,β-unsaturated carboxylic acid derivatives and α-halo-α,β-unsaturated aldehydes in high yields.
Preparation of enantiomerically pure sulfoxides from lactic acid and 3-hydroxybutyric acid. Isopropenyl tolyl sulfoxide and 2-(phenylsulfinyl)acrylate
Breitschuh,Seebach
, p. 1170 - 1178 (2007/10/02)
The EPC-synthesis of sulfoxides from readily available starting materials ('chiral pool') is demonstrated for the first time. Cyclic and open-chain thioethers derived from lactic and 3-hydroxybutyric acid are oxidized to sulfoxides, and the resulting prod
Substitution of 2-(Sulfonyloxy)carboxylates with Oxygene and Sulfur Nucleophiles without Racemization
Burkard, Ulrike,Effenberger, Franz
, p. 1594 - 1612 (2016/06/15)
The ethyl 2-(sulfonyloxy)propionates (S)-1a-c react with phenolates formed from 2 and with carboxylates 8 to give the respective 2-(aryloxy)- (R)-3 and 2-(acyloxy)propionates (R)-9 with inversion of configuration.Due to the high leaving tendency of the triflate group, (S)-1a generally give higher yields of substitution products under milder conditions than the corresponding mesylate (S)-1b and tosylate (S)-1c.In the case of the reaction of malic and succinic acid derivatives only the triflate (S)-10a is converted to the acyloxy compounds (R)-12 with carboxylates 8 atlow temperature (-45 deg C); with the mesylates 10b and the bromide 10d only elimination is observed.Mercaptides and thiophenolates formed from 17 react with (S)-1a-c analogously.With potassium thiocyanate 1a,b react almost exclusively to give the thiocyanate 19; only traces of the corresponding isothiocyanate 20 are obtained.
