36734-50-6Relevant academic research and scientific papers
Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid-Photoredox Hybrid Catalyst for the Generation of α-Carbonyl Radicals
Das, Sanju,Mandal, Tanumoy,De Sarkar, Suman
, p. 755 - 765 (2021/12/10)
A readily accessible organic-inorganic hybrid catalyst is reported for the reductive fragmentation of α-halocarbonyl compounds. The robust hybrid catalyst is a self-stabilizing combination of ZnCl2 Lewis acid and acridine orange as the photoactive organic dye. Mechanistic specifics of this hybrid catalyst have been studied in detail using both photophysical and electrochemical experiments. A systematic study enabled the discovery of the appropriate Lewis acid for the effective LUMO stabilization of α-halocarbonyl compounds and thereby lowering of reduction potential within the range of a standard organic dye. This strategy resolves the issues like dehalogenative hydrogenation or homo-coupling of alkyl radicals by guiding the photoredox cycle through an oxidative quenching pathway. The cooperativity between the photoactive organic dye and the Lewis acid counterparts empowers functionalization with a wide range of coupling partners through efficient and controlled generation of alkyl radicals and serves as an appropriate alternative to the expensive late transition metal-based photocatalysts. To demonstrate the application potential of this cooperative catalytic system, four different synthetic transformations of α-carbonyl bromides were explored with broad substrate scopes.
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
Preparation of Thioanisole Biscarbanion and C-H Lithiation/Annulation Reactions for the Access of Five-Membered Heterocycles
Zhu, Ranran,Liu, Zheyuan,Chen, Jie,Xiong, Xiaoyu,Wang, Yuntao,Huang, Lin,Bai, Jinshan,Dang, Yanfeng,Huang, Jianhui
supporting information, p. 3161 - 3165 (2018/06/11)
The synthesis, isolation, and X-ray structure of a thioanisole-based trilithium complex are reported. On the basis of the double-lithiation strategy, two novel synthetic methodologies have been developed under mild reaction conditions (room temperature): (1) reactions of lithiated thioanisoles with nitriles give benzoisothiazoles via a [3 + 2]-type of approach with two new bond formations and (2) formation of benzothiophenes from thioanisoles and amides through a [4 + 1] pattern forming 4 new chemical bonds.
A practical and chemoselective Mo-catalysed sulfoxide reduction protocol using a 3-mercaptopropyl-functionalized silica gel (MPS)
García, Nuria,Fernández-Rodríguez, Manuel A.,García-García, Patricia,Pedrosa, María R.,Arnáiz, Francisco J.,Sanz, Roberto
, p. 27083 - 27086 (2016/03/25)
A convenient sulfoxide deoxygenation procedure using a mercaptopropyl-functionalized silica gel as the reducing agent is described. This new protocol based on a heterogeneous reagent displays broad scope and tolerance to reducible functional groups and, from an experimental point of view, enhances previous methods by simplifying the isolation of the sulfide to a simple filtration.
Pinacol as a new green reducing agent: Molybdenum-catalyzed chemoselective reduction of sulfoxides and nitroaromatics
Garcia, Nuria,Garcia-Garcia, Patricia,Fernandez-Rodriguez, Manuel A.,Rubio, Ruben,Pedrosa, Maria R.,Arnaiz, Francisco J.,Sanz, Roberto
supporting information; experimental part, p. 321 - 327 (2012/04/11)
Pinacol is disclosed as a new chemoselective and environmentally benign reducing agent for sulfoxides and nitroaromatics assisted by readily available dichlorodioxomolybdenum(VI) complexes as catalysts. A wide range of substrates including those bearing challenging functional groups has been efficiently and selectively reduced with acetone and water being the only by-products of these reactions. 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
Ionic liquid promoted regio- and stereo-selective thiolysis of epoxides-A simple and green approach to β-hydroxy- and β-keto sulfides
Ranu, Brindaban C.,Mandal, Tanmay,Banerjee, Subhash,Dey, Suvendu S.
, p. 278 - 283 (2008/02/11)
A variety of epoxides underwent facile cleavage by thiols under the catalysis of 1-methyl-3-butylimidazolium bromide, [bmIm]Br, to produce the corresponding β-hydroxy sulfides with high regio- and stereo-selectivity. On the other hand, a specially designed basic ionic liquid, [bmIm]OH, efficiently catalyzes the thiolysis of ,β-epoxy ketones providing β-keto sulfides through simultaneous retro-aldol cleavages. The reactions are clean, high yielding, and do not require any organic solvent. The catalyst is also recycled. CSIRO 2007.
Selective deoxygenation of sulfoxides to sulfides with phosphites catalyzed by dichlorodioxomolybdenum(VI)
Sanz, Roberto,Escribano, Jaime,Aguado, Rafael,Pedrosa, Maria R.,Arnaiz, Francisco J.
, p. 1629 - 1632 (2007/10/03)
Chemoselective deoxygenation of sulfoxides to sulfides was carried out by P(OPh)3 in mild conditions catalyzed by dichlorodioxomolybdenum(VI).
Synthesis and calcium antagonistic activity of a series of diethyl benzofuryl, benzothienyl and benzogammapyronyl benzylphosphonates
Baziard-Mouysset, G.,Tchani, G. W.,Stigliani, J. L.,Payard, M.,Bonnafous, R.,Tisne-Versailles, J.
, p. 539 - 546 (2007/10/02)
In this work we present about 15 original heterocyclic diethyl benzylphosphonate analogues of fostedil, in which we have varied the nature of the heterocycle, the substituents or the phosphonic group, or even the position of this latter.Three diethyl 4-(2
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.
