96861-35-7Relevant academic research and scientific papers
Electrochemical oxidative radical oxysulfuration of styrene derivatives with thiols and nucleophilic oxygen sources
Wang, Yang,Deng, Lingling,Mei, Haibo,Du, Bingnan,Han, Jianlin,Pan, Yi
supporting information, p. 3444 - 3449 (2018/08/06)
Oxydifunctionalization of olefins represents a powerful tool and yet poses a challenging task. Previous methods have usually required a stoichiometric amount of a strong oxidant and an expensive transition-metal catalyst. This work describes the first example of the electrochemical oxysulfuration reaction of olefins with thiols and nucleophilic oxygen sources. This electrochemical difunctionalization reaction is conducted under catalyst- and oxidant-free conditions, and shows good substrate generality, affording thio-substituted alcohols, ethers and γ-lactones in good chemical yields and with excellent regioselectivities. This work represents a new and green strategy for the difunctionalization of olefins, and also provides a complementary and highly valuable prospect for current methodologies for the synthesis of thio-substituted compounds.
KI/K 2 S 2 O 8 -Mediated α-C-H Sulfenylation of Carbonyl Compounds with (Hetero)Aryl Thiols
Yang, Zan,Li, Jiao,Hua, Jie,Yang, Tao,Yi, Jianmin,Zhou, Congshan
supporting information, p. 2325 - 2329 (2017/10/06)
A new and facile KI/K 2 S 2 O 8 -mediated α-C-H sulfenylation of carbonyl compounds with (hetero)aryl thiols was developed for the formation of C-S bond at room temperature. This method provided a simple process for the sy
Visible light mediated reductions of ethers, amines and sulfides
Monos, Timothy M.,Magallanes, Gabriel,Sebren, Leanne J.,Stephenson, Corey R.J.
, p. 240 - 248 (2016/07/21)
Visible light-mediated photoredox catalysis enables the chemoselective reduction of activated carbon–heteroatom bonds as a function of reduction potential. The expansion of the scope of C–X bond reductions towards less activated motifs, such as ethers, amines and sulfides, is important to both organic synthesis and macromolecular degradation method development. In the present report, exploration of photoredox catalysis in alcoholic solvents mediated a decrease in the super-stoichiometric use of iPr2NEt and HCO2H in the reduction of α-keto ethers, amines and sulfides. Additionally, in the absence of fragmentation, [Formula presented] bond formation was afforded, suggesting an intermediate ketyl radicals are present in these transformations.
Catalyst-Free Insertion of Sulfoxonium Ylides into Aryl Thiols. A Direct Preparation of β-Keto Thioethers
Dias, Rafael M. P.,Burtoloso, Antonio C. B.
supporting information, p. 3034 - 3037 (2016/07/06)
Insertion of sulfoxonium ylides into the S-H bond of aryl thiols without the need for a catalyst is demonstrated, furnishing β-keto thioethers in excellent yield in most cases. The method overcomes traditional syntheses that employ metal catalysts in combination with diazo compounds or toxic and hard-prepared haloketones. The experimental setup consists of mixing the reagents in acetonitrile at room temperature. Additional experimental as well as kinetic isotopic effect studies give some insight into the mechanism of this reaction.
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
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
An efficient fluorination of β-ketosulfones promoted by a room-temperature ionic liquid at ambient conditions under ultrasound irradiation using Selectfluor F-TEDA-BF4
Heravi, Mohammad Reza Poor
body text, p. 1399 - 1402 (2011/10/08)
The fluorination reaction involving a β-ketosulfones by Selectfluor was efficiently promoted by the ionic liquid, [Hbim]BF4 (IL) as a reaction medium with methanol as co-solvent at room temperature under ultrasonic irradiation to afford the corresponding mono and difluoro-β-ketosulfones in excellent yields. The advantages of this method include among others the use of a recyclable, non-volatile ionic liquid, which promotes this protocol under room temperature without the requirement of any added catalyst under ultrasonic irradiation.
A practical and efficient route for the highly enantioselective synthesis of mexiletine analogues and novel β-thiophenoxy and pyridyl ethers
Huang, Kun,Ortiz-Marciales, Margarita,Stepanenko, Viatcheslav,De Jesus, Melvin,Correa, Wildeliz
, p. 6928 - 6931 (2008/12/22)
(Chemical Equation Presented) A practical and efficient procedure for the enantioselective synthesis of mexiletine analogues with use of 10% of spiroborate ester 6 as chirality transfer agent is presented. A variety of mexiletine analogues were prepared in good yield with excellent enantioselectivities (91-97% ee) from readily available starting materials. The developed methodology was also successfully applied for the synthesis of novel β-amino ethers containing thiophenyl and pyridyl fragments.
Novel synthesis of o-naphthothiophenequinone derivatives via regioselective Diels-Alder reaction
Shen, Yu-Dong,Wu, Hai-Qiang,Zhang, Sheng-Ling,Bu, Xian-Zhang,An, Lin-Kun,Huang, Zhi-Shu,Liu, Pei-Qing,Gu, Lian-Quan,Li, Yue-Ming,Chan, Albert S. C.
, p. 9097 - 9101 (2007/10/03)
A novel procedure to construct o-naphthothiophenequinones has been achieved from readily available o-benzothiophenquinones and N-dienes via Diels-Alder reaction-aromatization sequence as key steps. The absolute regioselectivity was established via Diels-A
A Facile One-Pot Synthesis of Alkyl Aryl Sulfides from Aryl Bromides
Ham, Jungyeob,Yang, Inho,Kang, Heonjoong
, p. 3236 - 3239 (2007/10/03)
A convenient one-pot synthetic method for the formation of alkyl aryl sulfides from various alkyl halides and lithium aryl thiolates that are prepared in situ by direct halogen-lithium exchange is reported. In particular, the method overcomes many of the problems encountered in previous reports; it is very quick, catalyst-free, and does not involve use of unstable aryl thiols.
