6178-58-1Relevant academic research and scientific papers
Synthesis and application of Cu(II) immobilized MCM-41 based solid Lewis acid catalyst for aminolysis reaction under solvent-free condition
Chaudhary, Garima,Gupta, Neha,Singh, Amit Pratap
, (2021/07/22)
In this paper, a Cu(II) immobilized periodic mesoporous organosilica (PMOs) was synthesized and used as a reusable solid Lewis acid catalyst for the aminolysis of epoxides under solvent-free conditions. An amide-based ligand, L-propylsilyl (1) having a specific binding pocket was prepared and fabricated on mesoporous MCM-41 to produce mesoporous organosilica L-propylsilyl@MCM-41 (2). Further, it has been utilized for anchoring Cu(II) ions under controlled reaction conditions to yield solid Lewis acid catalyst Cu(II)-L-propylsilyl@MCM-41 (3). The synthesized catalyst 3 exhibits significantly higher catalytic activity for aminolysis compared to hitherto known solid Lewis acid catalysts. An extensive range of β-amino alcohols with high regio and stereoselectivity were prepared by using catalyst 3. The catalyst was recovered easily and reused eight times without any loss in its catalytic activity. Furthermore, the synthesis of clinically significant propranolol (β-blocker) from α- naphthyl glycidyl ether was attained successfully using catalyst 3 in a very decent yield.
Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay
Wang, Shun,Cheng, Bei-Yi,Sr?en, Matea,K?nig, Burkhard
supporting information, p. 7524 - 7531 (2020/08/05)
The combination of photoredox catalysis with the Wolff-Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff-Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following the WK-type mechanism. With sulfur-centered radicals, the carbanions are further functionalized by reaction with electrophiles including CO2 and aldehydes, whereas CF3 radical addition furnishes a wide range of gem-difluoroalkenes through β-fluoride elimination of the generated α-CF3 carbanions. More than 80 substrate examples demonstrate the broad applicability of this reaction sequence. A series of investigations including radical inhibition, deuterium labeling, fluorescence quenching, cyclic voltammetry, and control experiments support the proposed radical-carbanion relay mechanism.
Biodegradable choline hydroxide promoted environmentally benign thiolysis of epoxides
Azizi, Najmedin,Edrisi, Mahtab
supporting information, p. 525 - 528 (2016/01/20)
An environmentally benign and rapid thiolysis of epoxides using a biodegradable, choline-based task-specific ionic liquid has been developed. The ring opening reaction of aryl and alkyl epoxides proceeded rapidly and afforded the corresponding β-hydroxysulfides in high yields with excellent regioselectivity. The protocol has the advantages of easy work-up, short reaction times, high yields, and a biodegradable catalyst.
Addition of unactivated thiols to epoxides and oxetanes catalyzed by a rhenium-oxo complex
Badiceanu, Alexandra D.,Garst, Alyson E.,Trubitt, Meredith E.,Nolin, Kristine A.
, p. 67 - 70 (2014/03/21)
A method for synthesizing β- and γ-hydroxy thioethers via addition of unactivated thiols to epoxides and oxetanes has been developed. This reaction is proposed to proceed through an unconventional mode of activation of the heterocycles. The transformation is catalyzed by ReO2I(PPh 3)2 affording β- and γ-hydroxy thioethers in moderate to excellent yield with excellent regioselectivity.
SULPHUR CONTAINING HIGH REFRACTIVE INDEX MONOMER
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Page/Page column 10-11, (2014/05/24)
This invention discloses aromatic based sulfur containing hydrophobic acrylate monomer with high refractive index. The invention further discloses process for the preparation of 2-phenyl-2-(phenylthio)ethyl acrylate of the formula (I). This monomer can be
Synthesis and evaluation of sulfonylethyl-containing phosphotriesters of 3′-azido-3′-deoxythymidine as anticancer prodrugs
Wang, Jiang,Wang, Yi-Jun,Chen, Zhe-Sheng,Kwon, Chul-Hoon
, p. 5747 - 5756 (2015/01/09)
A series of bis(sulfonylethyl) and mono(sulfonylethyl) phenyl phosphotriesters of zidovudine (3′-azido-3′-deoxythymidine, AZT) were synthesized as potential anticancer prodrugs that liberate AZT monophosphate via nonenzymatic β-elimination mechanism. Stab
Rapid, benign, and additive-free thiolysis of epoxides under ultrasonic/aqueous conditions
Mojtahedi, Mohammad M.,Khalili, Sajad
, p. 431 - 437 (2014/06/10)
An environmentally friendly and efficient procedure is developed for ring opening of various epoxides with thiols under non-thermal conditions. Reactions take place by ultrasonic irradiation of the two reactants suspended in an additive-free aqueous mediu
In situ slow release of isocyanates: Synthesis and organocatalytic application of N-acylureas
Singh, Atul K.,Chawla, Ruchi,Yadav, Lal Dhar S.
, p. 5099 - 5102 (2013/09/02)
A novel, efficient, and operationally simple one-pot synthesis of both, symmetrical and unsymmetrical N-acylureas from carboxamides and in situ generated isocyanates (from N,N-dibromo-p-toluenesulfonamide) in the presence of a mild base at rt is reported. The protocol avoids the tedious isolation and purification steps of hazardous isocyanates. The first application of these acylureas to the catalysis through hydrogen bonding is also demonstrated.
" On-water " thiolysis of epoxides promoted by PhSZnBr
Propersi, Simona,Tidei, Caterina,Bagnoli, Luana,Marini, Francesca,Testaferri, Lorenzo,Santi, Claudio
, p. 671 - 676 (2014/01/06)
The synthesis of a new bench-stable and odorless zinc thiolate is here reported. The thiolysis of epoxides effected using this reagent showed a considerable rate acceleration of the reaction when effected in "on-water" conditions. In addition, the reactio
Kinetic resolution of α-bromophenylacetamides using quinine or Cinchona alkaloid salts
Marzorati, Liliana,Fejfar, Jose L.,Tormena, Claudio F.,Vitta, Claudio Di
experimental part, p. 748 - 753 (2012/09/05)
The kinetic resolution of racemic α-bromophenylacetamides 1 was achieved in the presence of benzenethiolate and Cinchona alkaloid salts as phase-transfer catalysts or benzenethiol and quinine, yielding (S)-enantioenriched α-sulfanylated products. The observed stereoselection was rationalized on the basis of the best fitting of 1 and the resolving agent in the ternary complexes.
