- Carbenium ion formation by fragmentation of electrochemically generated oxonium ions
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Fragmentation of electrochemically generated oxonium ions can be exploited to form carbenium ions at a low oxidation potential in the presence of a nucleophile. The application of this concept is demonstrated for the allylation of carbenium ions generated by the anodic oxidation of stannylmethylethers.
- Lielpetere, Anna,Jirgensons, Aigars
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supporting information
p. 5094 - 5096
(2018/07/29)
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- P4VPy–CuO nanoparticles as a novel and reusable catalyst: application at the protection of alcohols, phenols and amines
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P4VPy–CuO nanoparticles were synthesized using ultrasound irradiations. Relevant properties of the synthesized nanoparticles were investigated by X-ray diffraction, scanning electron microscopy, transmission electron microscopy and Fourier transform infrared spectroscopy. After identification, the prepared reagent was used for the promotion of different types of protection reactions of alcohols, phenols and amines. Easy workup, short reaction times, excellent yields, relatively low cost and reusability of the catalyst are the striking features of the reported methods.
- Shirini, Farhad,Fallah-Shojaei, Abdollah,Abedini, Masoumeh,Samavi, Laleh
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p. 1699 - 1712
(2016/07/27)
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- Traceless directing group for stereospecific nickel-catalyzed alkyl-alkyl cross-coupling reactions
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Stereospecific nickel-catalyzed cross-coupling reactions of benzylic 2-methoxyethyl ethers are reported for the preparation of enantioenriched 1,1-diarylethanes. The 2-methoxyethyl ether serves as a traceless directing group that accelerates cross-coupling. Chelation of magnesium ions is proposed to activate the benzylic C-O bond for oxidative addition.
- Greene, Margaret A.,Yonova, Ivelina M.,Williams, Florence J.,Jarvo, Elizabeth R.
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supporting information; experimental part
p. 4293 - 4296
(2012/09/22)
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- H3PW12O40at the[bmim][FeCl4]: A green catalytic system for alkoxymethylation of alcohols and their one-pot interconversion to acetates and TMS-ethers
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12-Tungstophosphoric acid immobilized on [bmim][FeCl4] was found to be an efficient catalyst for chemoselective methoxymethylation and ethxoymethylation of alcohols and also one-pot conversion of MOM- or EOM-ethers to their corresponding acetates and TMS-ethers under thermal conditions and microwave irradiation. These procedures were simple, rapid and the corresponding products were obtained in high yields. The catalyst exhibited remarkable reactivity and was reusable.
- Mohammadpoor-Baltork,Moghadam,Tangestaninejad,Mirkhani,Khosropour,Mirjafari
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experimental part
p. 513 - 524
(2012/06/16)
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- [InCl4]: An efficient catalyst-medium for alkoxymethylation of alcohols and their interconversion to acetates and TMS-ethers
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A simple, green and chemoselective method for methoxymethylation and ethoxymethylation of primary and secondary alcohols using a Lewis acidic room temperature ionic liquid, [C4mim][InCl4], as catalyst and reaction medium under ambient temperature, microwave and ultrasonic irradiations is reported. In this catalytic system, the corresponding MOM-and EOM-ethers are obtained in excellent yields and in short reaction times. Furthermore, this catalytic system was used for mild and efficient transformations of these protected alcohols to their corresponding acetates and trimethylsilyl ethers under thermal conditions and microwave and ultrasonic irradiations.
- Mohammadpoor-Baltork, Iraj,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Khosropour, Ahmad Reza,Mirjafari, Arsalan
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experimental part
p. 568 - 579
(2012/05/05)
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- A mild and efficient method for the methoxymethylation and acetylation of alcohols promoted by benzyltriphenylphosphonium tribromide
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A mild and efficient method for the conversion of alcohols to their corresponding methoxymethyl ethers and acetates using benzyltriphenylphosphonium tribromide (BTPTB) as catalyst is described. All reactions were performed under completely heterogeneous reaction conditions in good to high yields.
- Shirini, Farhad,Imanzadeh, Gholam Hossein,Mousazadeh, Seyyed Ali Reza,Mohammadpoor-Baltork, Iraj,Abedin, Masoumeh
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experimental part
p. 1187 - 1190
(2011/10/05)
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- H3PW12O40 - A selective, environmentally benign, and reusable catalyst for the preparation of methoxymethyl and ethoxymethyl ethers and their deprotections under mild conditions
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Different types of primary and secondary alcohols were efficiently transformed to their corresponding methoxymethyl (MOM) and ethoxymethyl (EOM) ethers in the presence of catalytic amounts of H3PW 12O40 at room temperature under solvent-free conditions. Selective protection of primary and secondary alcohols in the presence of phenols and tertiary alcohols was achieved by this method. Deprotection of these ethers to their parent alcohols was also performed using this catalyst in ethanol under reflux conditions. We have also found that primary and secondary MOM- and EOM-ethers are selectively deprotected in the presence of phenolic and tertiary ones, methyl and benzyl ethers, esters, and trimethylsilyl ethers by this catalyst. The notable advantages of this protocol are high yields, short reaction times, easy work-up, non-toxicity, easy availability and handling, eco-friendly, and reusability of the catalyst.
- Mohammadpoor-Baltork, Iraj,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mirjafari, Arsalan
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p. 831 - 840
(2008/12/21)
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- N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide and poly(N-bromo-N-ethyl-benzene-1,3-disulfonamide) as efficient catalysts for the methoxymethylation of alcohols under solvent-free conditions
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Methoxymethylation of a variety of alcohols was performed using formaldehyde dimethyl acetal in the presence of N,N,N′,N′- tetrabromobenzene-1,3-disulfonamide [TBBDA] and poly(N-bromo-N-ethyl-benzene-1, 3-disulfonamide) [PBBS] as catalysts at room tempera
- Ghorbani-Vaghei, Ramin,Zolfigol, Mohammad Ali,Amiri, Mostafa,Veisi, Hojat
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experimental part
p. 632 - 635
(2009/05/07)
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- Metal hydrogen sulfates catalyzed methoxymethylation of alcohols under solvent-free conditions
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Methoxymethylation of a variety of alcohols was performed by using formaldehyde dimethoxy acetal in the presence of metal hydrogen sulfate M(HSO4)n at room temperature and solvent-free conditions. The methoxymethyl ethers (MOM-ethers
- Niknam, Khodabakhsh,Zolfigol, Mohammad Ali,Shayegh, Mohsen,Zare, Reza
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p. 1067 - 1073
(2008/02/13)
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- Molybdatophosphoric acid as a catalyst for the methoxymethylation of alcohols under solvent-free conditions
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The methoxymethylation of alcohols was performed using formaldehyde dimethoxy acetal in the presence of H3PMo12O 40·xH2O at room temperature under solvent-free conditions.
- Zolfigol, Mohammad Ali,Shiri, Morteza
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p. 165 - 166
(2007/10/03)
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- An efficient protocol for the preparation of MOM ethers and their deprotection using zirconium(IV) chloride
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An efficient protocol for the preparation of MOM ethers from alcohols and formaldehyde dimethyl acetal (DMFA) using ZrCl4 (10 mol %) at room temperature under solvent free conditions has been developed. Similarly, the same Lewis acid, ZrCl4 (50 mol %), in isopropanol at reflux was utilised for the deprotection of MOM ethers. An efficient protocol for the preparation of MOM ethers from alcohols and formaldehyde dimethyl acetal (DMFA) using ZrCl4 (10 mol %) at room temperature under solvent free conditions has been developed. Similarly, the same Lewis acid, ZrCl4 (50 mol %), in isopropanol at reflux was utilised for the deprotection of MOM ethers.
- Sharma,Reddy, K. Laxma,Sree Lakshmi,Radha Krishna, Palakodety
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p. 9229 - 9232
(2007/10/03)
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- Methoxymethylation of alcohols, phenols, and avermectin aglycones using MOM-2-pyridylsulfide
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Methoxymethyl-2-pyridylsulfide (MOM-ON) is an effective methoxymethylating reagent when used in conjunction with AgOTf, NaOAc, and THF. A wide range of MOM ethers are produced from corresponding phenols and alcohols, including tertiary and allylic alcohols, in good yields and under mild, neutral conditions. This method is also effective for the methoxymethylation of avermectin aglycones.
- Marcune,Karady,Dolling,Novak
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p. 2446 - 2449
(2007/10/03)
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