- Silver/NBS-Catalyzed Synthesis of α-Alkylated Aryl Ketones from Internal Alkynes and Benzyl Alcohols via Ether Intermediates
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The silver hexafluoroantimonate/N-bromosuccinimide (NBS)-catalyzed synthesis of α-alkylated aryl ketones with a tertiary carbon center from internal alkynes and benzyl alcohols is reported. This reaction proceeds via the etherification of benzyl alcohols with an in situ generated benzyl bromide, formed by the reaction of benzyl alcohol with a catalytic amount of NBS and AgSbF6. Ag-catalyzed C-O cleavage of the ether leads to a tolyl radical, which undergoes addition to the alkyne, ultimately leading to the α-alkylated aryl ketone products.
- Chun, Supill,Chung, Young Keun
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supporting information
p. 5583 - 5586
(2018/09/21)
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- Fluorodecarboxylation, rearrangement and cyclisation: the influence of structure and environment on the reactions of carboxylic acids with xenon difluoride
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The reactions of structurally diverse carboxylic acids with XeF2 in both CH2Cl2/Pyrex and CH2Cl2/PTFE have been studied. Pyrex appears to be a very effective heterogeneous catalyst for an electrophilic mode of reaction of polarised XeF2, leading to rearrangement, cyclisation and cationic products. In CH2Cl2/PTFE, fluorodecarboxylation is the main mode of reaction, in accordance with previous studies, and may occur via a SET reaction of unpolarised XeF2.
- Ramsden, Christopher A.,Shaw, Maxine M.
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experimental part
p. 3321 - 3324
(2009/08/09)
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- High-efficiency conversion of trimethylsilyl ethers to their corresponding ethers using carbon-based solid acid as a new catalyst in heterogeneous mixtures
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Carbon-based solid acid was used as a new catalyst for conversion of trimethylsilyl ethers to their corresponding ethers in heterogeneous mixtures. The experiments were done moderately at room temperature, and high yields in suitable times were obtained under these conditions. Copyright Taylor & Francis Group, LLC.
- Shokrollahi, Arash,Zali, Abbas,Pouretedal, Hamid Reza
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p. 371 - 375
(2008/04/01)
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- Silica Sulfuric Acid: An Efficient Catalyst for the Direct Conversion of Primary and Secondary Trimethylsilyl Ethers to their Corresponding Ethers under Mild and Heterogeneous Conditions
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Primary and secondary trimethylsilyl ethers were converted to their corresponding ethers in the presence silica sulfuric acid with good to excellent yields under mild and heterogeneous conditions.
- Zolfigol, Mohammad Ali,Mohammadpoor-Baltork, Iraj,Mirjalili, Bibi Fatemeh,Bamoniri, Abdolhamid
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p. 1877 - 1879
(2007/10/03)
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- The use of Nafion-H as an efficient catalyst for the direct conversion of primary and secondary trimethylsilyl ethers to their corresponding ethers under mild and heterogeneous conditions
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Primary and secondary trimethylsilyl ethers were converted to their corresponding ethers in the presence Nafion-H with good to excellent yields under mild and heterogeneous conditions.
- Zolfigol, Mohammad Ali,Mohammadpoor-Baltork, Iraj,Habibi, Davood,Mirjalili, BiBi Fatemeh,Bamoniri, Abdolhamid
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p. 8165 - 8167
(2007/10/03)
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- Unidirectional Dieckmann Cyclizations on a Solid Phase and in Solution
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Dieckmann cyclization of 2percent divinylbenzene-copolystyrene resin alkyl pimelates and analogous benzyl alkyl pimelates is reported.The use of uniquely single-labeled dioate esters has allowed analysis of the direction of closure via decarboxylation of the keto ester products.The influence of steric factors on the competition between enolate condensation and transesterification and upon the direction of closure of the cyclization has been evaluated, and the conditions for achieving >99percent regioselective closure are described.Modifications in the conditions of solid-phase peptide synthesis required for successful high-temperature enolate cyclization have been developed and the results are compared to solution reactions of benzyl alkyl esters under similar conditions.The resin attachment afforded a clear benefit over the benzyl models and greatly simplified isolation and purification of the resulting β-keto esters.
- Crowley, John I.,Rapoport, Henry
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p. 3215 - 3227
(2007/10/02)
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