14032-04-3Relevant articles and documents
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
supporting information, (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.
Lithium BINOL phosphate catalyzed desymmetrization of meso-epoxides with aromatic thiols
Ingle, Gajendrasingh,Mormino, Michael G.,Antilla, Jon C.
supporting information, p. 5548 - 5551 (2015/02/19)
A highly enantioselective method for desymmetrization of meso-epoxides using thiols is reported. This is the first example of epoxide activation achieved using metal BINOL phosphates. The reaction has a broad scope in terms of epoxide substrates and aroma
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
Amberlyst-15: An efficient heterogeneous reusable catalyst for selective anti-Markovnikov addition of thiols to alkenes/alkynes and for thiolysis of epoxides
Lanke, Satish R.,Bhanage, Bhalchandra M.
, p. 29 - 33 (2013/08/23)
The anti-Markovnikov addition of thiols to alkenes/alkynes and thiolysis of epoxides is described using Amberlyst-15 as a selective, commercially available, inexpensive and reusable catalyst. The products like diorganyl sulphides, β-hydroxy sulphides and phenyl(styryl)sulfanes were obtained in good to excellent yields in short reaction time and with high regio-selectivity. The catalyst was reused up to five consecutive recycles without any loss in its catalytic activity. The developed methodology is a metal free protocol for C-S bond formation reaction with high atom economy.
Highly enantioselective kinetic resolution of trans-2-(phenylthio) cyclohexanol derivatives by immobilized Candida antartica B lipase
Chimni, Swapandeep Singh,Kaur, Kirandeep,Bala, Neeraj
, p. 67 - 74 (2013/10/22)
Candida antartica B (immobilized CAL-B) mediated resolutions of trans-2-(phenylthio)cyclohexanol derivatives using vinyl acetate as acylating agent and MTBE as solvent provide excellent enantioselectivity (up to >99%) and high yield of both the enantiomer
Recyclable superparamagnetic Fe3O4 nanoparticles for efficient catalysis of thiolysis of epoxides
Mojtahedi, Mohammad M.,Abaee, M. Saeed,Rajabi, Azam,Mahmoodi, Peyman,Bagherpoor, Saeed
experimental part, p. 68 - 71 (2012/08/07)
An efficient and rapid procedure is developed for room-temperature ring opening of various epoxides with thiols under solvent-free conditions in the presence of catalytic amount of superparamagnetic Fe3O4 nanoparticles. As a result,
JandaJel as a polymeric support to improve the catalytic efficiency of immobilized-1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) under solvent-free conditions
Lanari, Daniela,Ballini, Roberto,Bonollo, Simona,Palmieri, Alessandro,Pizzo, Ferdinando,Vaccaro, Luigi
supporting information; experimental part, p. 3181 - 3186 (2011/12/04)
JandaJel, with its greater spacing between the linear polymeric chains compared to that of polystyrene matrices, is a very efficient support for improving the catalytic efficiency of TBD under SolFC. The Royal Society of Chemistry.
LiOH-catalyzed simple ring opening of epoxides under solvent-free conditions
Azizi, Najmedin,Khajeh-Amiri, Alireza,Ghafuri, Hossein,Bolourtchian, Mohammad
scheme or table, p. 1550 - 1557 (2010/09/06)
LiOH has been found to be a very simple and selective catalyst for the rapid and mild synthesis of β-hydroxy sulfides and β-hydroxyl nitriles by ring opening of epoxides with aromatic, aliphatic, and heterocyclic thiols and trimethylsilyl cyanide at room temperature under solvent free conditions. All the reactions proceeded satisfactorily in short times and afforded the corresponding products in good to excellent yields with high regioselectivity and chemoselectivity under mild reaction conditions. Copyright Taylor & Francis Group, LLC.
One-pot synthesis of β-amino/β-hydroxy selenides and sulfides from aziridines and epoxides
Ganesh, Venkataraman,Chandrasekaran, Srinivasan
experimental part, p. 3267 - 3278 (2010/02/27)
Diaryl disulfides and diselenides undergo facile cleavage on treatment with rongalite (sodium hydroxymethanesulfinate) to generate the corresponding thiolate and selenolate species in situ, which effect the ring opening of aziridines and epoxides in a reg
Erbium(III) triflate is a highly efficient catalyst for the synthesis of β-alkoxy alcohols, 1,2-diols and β-hydroxy sulfides by ring opening of epoxides
Dalpozzo, Renato,Nardi, Monica,Oliverio, Manuela,Paonessa, Rosina,Procopio, Antonio
experimental part, p. 3433 - 3438 (2010/02/28)
Chemo- and stereoselectivity in the ring-opening reaction of epoxides with erbium(III) triflate are described. Epoxides can be cleaved under neutral conditions with alcohols and thiols in the presence of catalytic amounts of Lewis acid, affording the corresponding β-alkoxy alcohols and β-hydroxy sulfides in high yields. In water, epoxide ring opening occurs to produce the corresponding diols in good yields.
