105966-39-0Relevant articles and documents
Solvent-free NaHSO4-SiO2-catalyzed efficient tetrahydropyranylation of alcohols and phenols
Kinfe, Henok H.,Mebrahtu, Fanuel M.,Moshapo, Paseka T.
, p. 1237 - 1242 (2013)
A simple and efficient tetrahydropyranylation of alcohols and phenols has been developed using NaHSO4-SiO2 (0.5 mol%) as a catalyst under solvent-free conditions to yield corresponding tetrahydropyranyl ethers in excellent yields.
Cyclopropenium Enhanced Thiourea Catalysis
Smajlagic, Ivor,Durán, Rocio,Pilkington, Melanie,Dudding, Travis
, p. 13973 - 13980 (2018)
An integral part of modern organocatalysis is the development and application of thiourea catalysts. Here, as part of our program aimed at developing cyclopropenium catalysts, the synthesis of a thiourea-cyclopropenium organocatalyst with both cationic hydrogen-bond donor and electrostatic character is reported. The utility of the this thiourea organocatalyst is showcased in pyranylation reactions employing phenols, primary, secondary, and tertiary alcohols under operationally simple and mild reaction conditions for a broad substrate scope. The addition of benzoic acid as a co-catalyst facilitating cooperative Br?nsted acid catalysis was found to be valuable for reactions involving phenols and higher substituted alcohols. Mechanistic investigations, including kinetic and 1H NMR binding studies in conjunction with density function theory calculations, are described that collectively support a Br?nsted acid mode of catalysis.
Efficient tetrahydropyranyl and tetrahydrofuranyl protection/deprotection of alcohols and phenols with Al(OTf)3 as catalyst
Williams, D. Bradley G.,Simelane, Sandile B.,Lawton, Michelle,Kinfe, Henok H.
, p. 4573 - 4576 (2010)
A simple and efficient method for the conversion of alcohols and phenols into their corresponding THP and THF ethers at room temperature has been developed using 1 mol % aluminium triflate as catalyst. The deprotection reaction in the presence of methanol using Al(OTf)3 was equally successful and could be performed at ambient temperature in high yields.
Efficient trimethylsilylation and tetrahydropyranylation of alcohols in the presence of 1,3-dibromo-5,5-dimethylhydantoin
Shirini, Farhad,Zolfigol, Mohammad Ali,Paktinat, Maryam
, p. 4252 - 4256 (2006)
Chemoselective trimethylsilylation and tetrahydropyranylation of benzylic and primary and secondary aliphatic alcohols proceed efficiently in the presence of 1,3-dibromo-5,5-dimethylhydantoin (DBH) under mild and completely heterogeneous reaction conditio
Silica-gel-supported aluminium chloride: A stable, efficient, selective, and reusable catalyst for tetrahydropyranylation of alcohols and phenols
Borujeni, Kaveh Parvanak
, p. 2705 - 2710 (2006)
A simple, effective, and highly chemoselective method to form 2-tetrahydropyranyl ethers of alcohols and phenols in the presence of silica-gel-supported aluminium chloride as a heterogeneous Lewis acid catalyst is described. The catalyst can be easily recovered and reused without appreciable change in its efficiency. Copyright Taylor & Francis Group, LLC.
An efficient Br?nsted–Lewis acidic ionic liquid catalyzed tetrahydropyranylation of alcohols
Azizi, Najmedin,Abdoli-Senejani, Masumeh,Abbasi, Faezeh
, p. 5009 - 5011 (2016)
An imidazolium based Br?nsted–Lewis acidic ionic liquid has been shown to be an excellent catalyst and reaction medium for the tetrahydropyranylation of various alcohols in good to excellent yields with short reaction times. Selective protection of benzyl
Dowex 50WX4-100: An efficient catalyst for the tetrahydropyranylation of alcohols
Poon,Banerjee, Ajoy K.,Bedoya, Liadis,Laya, Manuel S.,Cabrera, Elvia V.,Albornoz, Karla M.
, p. 3369 - 3377 (2009)
The ion-exchange resin Dowex 50WX4-100 has been found to catalyze efficiently the protection reaction of a variety of alcohols with 2,3-dihydro-4H pyran (DHP) and dichloromethane at ambient conditions. Copyright Taylor & Francis Group, LLC.
Short communication: Catalytic tetrahydropyranylation of phenols and alcohols using vanadium(V)-substituted polyoxomolybdates
Gharib, Ali,Jahangir, Manouchehr
, p. 287 - 296 (2012)
Alcohols and phenols were tetrahydropyranylated in the presence of H 7[PMo8V4O40] in good to excellent yields in acetonitrile and under solventfree reaction conditions. A mild and convenient method for the formation and deprotection of ethers (THP ethers) is described. The formation of THP ethers from the corresponding alcohols was accomplished in the presence of acid-sensitive functional groups.
Direct Conversion of TMS-ethers to THP-ethers Catalyzed by {[K.18-Crown-6]Br3}n
Chehardoli, Gholamabbas,Zolfigol, Mohammad Ali,Derakhshanpanah, Fateme
, p. 192 - 197 (2019/04/27)
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Zwitterionic imidazolium salt: An efficient organocatalyst for tetrahydropyranylation of alcohols
Mahato, Sachinta,Chatterjee, Rana,Chakraborty Ghosal, Nirnita,Majee, Adinath
supporting information, p. 1905 - 1915 (2017/10/07)
An aprotic imidazole based zwitterionic-salt, 4-(3-methylimidazolium)-butane sulfonate has been found to be an efficient organocatalyst for tetrahydropyranylation by the reaction of 3,4-dihydro-2H-pyran (DHP) and different aliphatic alcohols as well as various phenolic compounds. The notable advantages of the present method are general applicability to various alcohols, clean reaction, production of no hazardous waste, open air reaction conditions and high yields. The catalyst can be reused without the loss of significant catalytic activity.
