5331-14-6Relevant articles and documents
Silver(I)-Catalyzed Reductive Cross-Coupling of Aldehydes to Structurally Diverse Cyclic and Acyclic Ethers
Dong, Guichao,Li, Chuang,Liang, Ting,Xu, Xin,Xu, Zhou
supporting information, p. 1817 - 1821 (2022/03/16)
A range of medium-sized cyclic ethers (5 to 11 membered) have been effectively synthesized through intramolecular reductive coupling of dialdehydes initiated by 50 ppm to 0.5% of AgNTf2 with hydrosilane at 25 °C. The catalytic system is also suitable for the coupling of two different monoaldehydes to provide unsymmetrical ethers. This protocol features broad functional group compatibility, high product diversity, high efficiency, and utility in the late-stage modification of complex biorelevant molecules.
Photocatalytic nucleophilic addition of alcohols to styrenes in Markovnikov and anti-Markovnikov orientation
Weiser, Martin,Hermann, Sergej,Penner, Alexander,Wagenknecht, Hans-Achim
, p. 568 - 575 (2015/06/08)
The nucleophilic addition of methanol and other alcohols to 1,1-diphenylethylene (1) and styrene (6) into the Markovnikov- and anti-Markovnikov-type products was selectively achieved with 1-(N,N-dimethylamino)pyrene (Py) and 1,7-dicyanoperylene-3,4:9,10-tetracarboxylic acid bisimide (PDI) as photoredox catalysts. The regioselectivity was controlled by the photocatalyst. For the reductive mode towards the Markovnikov-type regioselectivity, Py was applied as photocatalyst and triethylamine as electron shuttle. This approach was also used for intramolecular additions. For the oxidative mode towards the anti-Markovnikov-type regioselectivety, PDI was applied together with Ph-SH as additive. Photocatalytic additions of a variety of alcohols gave the corresponding products in good to excellent yields. The proposed photocatalytic electron transfer mechanism was supported by detection of the PDI radical anion as key intermediate and by comparison of two intramolecular reactions with different electron density. Representative mesoflow reactor experiments allowed to significantly shorten the irradiation times and to use sunlight as "green"light source.
Synthesis of ethers from esters via Fe-catalyzed hydrosilylation
Das, Shoubhik,Li, Yuehui,Junge, Kathrin,Beller, Matthias
supporting information, p. 10742 - 10744 (2013/01/15)
Triiron dodecacarbonyl allows for the selective reduction of esters into the corresponding ethers. This protocol has a wide substrate scope. In addition, cholesteryl pelarogonate has been reduced under the reaction conditions with an excellent yield.
Direct reduction of esters to ethers with an indium(III) bromide/triethylsilane catalytic system
Sakai, Norio,Moriya, Toshimitsu,Fujii, Kohji,Konakahara, Takeo
experimental part, p. 3533 - 3536 (2009/05/07)
An indium(III) bromide-triethylsilane reagent system promotes direct reduction of esters to produce the corresponding unsymmetrical ethers. This simple catalytic system accommodated other carbonyl compounds, such as a tertiary amide and a carboxylic acid. Georg Thieme Verlag Stuttgart.
An efficient one-pot synthesis of unsymmetrical ethers: A directly reductive deoxygenation of esters using an InBr3/Et3SiH catalytic system
Sakai, Norio,Moriya, Toshimitsu,Konakahara, Takeo
, p. 5920 - 5922 (2008/02/09)
(Chemical Equation Presented) This study describes a novel one-pot procedure for a directly reductive conversion of the carbonyl function of esters to the corresponding ethers by Et3SiH in the presence of a catalytic amount of InBr3.
Indium(III) chloride-sodium borohydride system: A convenient radical reagent for an alternative to tributyltin hydride system
Inoue, Katsuyuki,Sawada, Akemi,Shibata, Ikuya,Baba, Akio
, p. 906 - 907 (2007/10/03)
The indium hydride generated from NaBH4 and InCl3, is a promising candidate of alternative to Bu3SnH. In particular, the catalytic performance of InCl3 in the dehalogenation of alkyl and aryl halides, intramolecular cyclization and intermolecular coupling reaction are noteworthy. Copyright
FLUORIDE SALTS ON ALUMINA AS REAGENTS FOR ALKYLATION OF PHENOLS AND ALCOHOLS.
ANDO,YAMAWAKI,KAWATE,SUMI,HANAFUSA
, p. 2504 - 2507 (2007/10/02)
THE EFFECTIVENESS OF ALKALI METAL FLUORIDES IMPREGNATED ON ALUMINA AS A REAGENT FOR PROMOTING ALKYLATION WAS OPTIMIZED WITH RESPECT TO THE METAL CATION, THE AMOUNT OF IMPREGNATION, AND THE REACTION SOLVENT. POTASSIUM OR CAESIUM FLUORIDE ONALUMINA IN ACETONITRILE OR 1,2-DIMETHOXYETHANE WAS CONCLUDED TO BE THE BEST REACTION SYSTEM FOR GENERAL USE. O-ALKYLATION OF SUBSTITUTED PHENOLS, PRIMARY AND SECONDARY ALCOHOLS, AND A GLYCOL WAS CARRIED OUT MOSTLY IN GOOD YIELDS UNDER MILDCONDITIONS WITH SIMPLE EXPERIMENTAL PROCEDURES.