- Study of O-allylation using triazine-based reagents
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Acid-catalyzed allylating reagent 2,4,6-tris(allyloxy)-1,3,5-triazine (TriAT-allyl) and its substituted derivatives have been developed. The reaction of acid-, and alkali-labile alcohols with these reagents in the presence of a catalytic amount of trifluoromethanesulfonic acid (TfOH) afforded the corresponding allyl ethers in good yields. Reactions using these reagents with an unsymmetrically-substituted regioisometric allyl group suggested that a single isometric allylic cation species would be involved.
- Yamada, Kohei,Hayakawa, Naoko,Fujita, Hikaru,Kitamura, Masanori,Kunishima, Munetaka
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p. 112 - 115
(2017/01/06)
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- Oxidation of acyclic alkenes and allyl and benzyl ethers with DIB/t-BuOOH/Mg(OAc)2
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Oxidation of (11Z)-1′,2′-didehydrostemofoline with DIB/TBHP/Mg(OAc)2·4H2O resulted in oxidative cleavage of the C-11-C-12 double bond instead of the desired allylic oxidation of the 1-butenyl side chain. Stemofoline gave a similar result. The oxidation of more simple terminal alkenes was regioselective and gave vinyl ketones while allyl and benzyl ethers gave acrylate and benzoate esters, respectively. Allyl and benzyl ethers could be chemoselectively oxidized in the presence of a terminal alkene or benzyl group. Oxidation of an internal alkene was poorly regioselective, in contrast to the oxidation of 1-substituted cyclohexenes.
- Sastraruji, Thanapat,Pyne, Stephen G.,Ung, Alison T.
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body text
p. 598 - 602
(2012/01/05)
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- One-pot sequential synthesis of ethers from an aliphatic carboxylic acid and an alcohol by indium-catalyzed deoxygenation of an ester
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We have developed a widely applicable and direct method of etherification from a carboxylic acid and an alcohol by indium-catalyzed deoxygenation of the transient ester formed in a one-pot reaction. This simple catalytic reducing system appears to be remarkably tolerant of several functional groups including alkenes, halogens, nitro and heterocyclic groups. A reducing system composed of InBr3 and an economical hydrosiloxane, PMHS (polymethylhydrosiloxane) , enabled one-pot etherification by using a variety of aliphatic carboxylic acids and alcohols. Copyright
- Sakai, Norio,Usui, Yuta,Moriya, Toshimitsu,Ikeda, Reiko,Konakahara, Takeo
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p. 4603 - 4608
(2012/10/30)
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- A highly efficient method for the reductive etherification of carbonyl compounds with triethylsilane and alkoxytrimethylsilane catalyzed by iron(III) chloride
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Facile reductive etherification of carbonyl compounds can be conveniently performed by reaction with triethylsilane and alkoxytrimethylsilane catalyzed by iron(III) chloride. The corresponding alkyl ethers, including benzyl and allyl ethers, of the reduced alcohols were obtained in good to excellent yields under mild reaction conditions.
- Iwanami, Katsuyuki,Seo, Hana,Tobita, Yuki,Oriyama, Takeshi
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p. 183 - 186
(2007/10/03)
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- General method for the palladium-catalyzed allylation of aliphatic alcohols
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A palladium catalysis-mediated approach to coupling aliphatic alcohols with allyl carbonates has been developed. The method allows for the allylation of primary, secondary, and tertiary alcohols efficiently under mild conditions. Limitations were explored as well as the asymmetric application of the chemistry. Regiochemical and olefin geometry was controlled in the coupling of unsymmetrical allylating agents. Transient allyl carbonates were observed in the coupling, which comprised the trans-carboxylation of the allyl-carbonate with the requisite alcohol.
- Haight, Anthony R.,Stoner, Eric J.,Peterson, Matthew J.,Grover, Vandana K.
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p. 8092 - 8096
(2007/10/03)
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- AlCl3-N,N-Dimethylaniline: A Novel Benzyl and Allyl Ether Cleavage Reagent
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A combination system of AlCl3-N,N-dimethylaniline was found to cleave benzyl ethers readily to give parent alcohols in excellent yields.The system also cleaved allyl as well as methyl ethers.Numerous functional groups such as benzoyloxy, phenylthio, and olefinic double bond were not affected.Comparison of AlCl3-N,N-dimethylaniline and AlCl3-anisole were described.
- Akiyama, Takahiko,Hirofuji, Hajimu,Ozaki, Shoichiro
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p. 1932 - 1938
(2007/10/02)
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