65299-82-3Relevant articles and documents
Iodine catalysed synthesis of unsymmetrical benzylic ethers by direct cross-coupling of alcohols
Kharrngi, Balamphrang,Basumatary, Grace,Bez, Ghanashyam
supporting information, (2021/09/13)
Although symmetrical ethers can be synthesized easily from alcohols, synthesis of unsymmetrical ethers by dehydrative cross-coupling of alcohols is still a challenge. While dehydrative cross-coupling is environmentally appealing due to formation of water as the only byproduct, the chances for formation of symmetrical ethers always exist. The existing transition metal based methods give good selectivity, but the catalyst are costly and not readily available. Here, we present a simple, readily available, and cost-effective catalyst in the form of molecular iodine which catalyzes a highly selective cross-coupling of benzylic alcohols with benzyl, alkyl, and aryl alcohols to give their corresponding unsymmetrical ethers in good to excellent yield.
Reductive Etherification of Aldehydes and Ketones with Alcohols and Triethylsilane Catalysed by Yb(OTf)3: an Efficient One-Pot Benzylation of Alcohols
Pelosi, Azzurra,Lanari, Daniela,Temperini, Andrea,Curini, Massimo,Rosati, Ornelio
supporting information, p. 4527 - 4539 (2019/08/26)
The one-pot synthesis of symmetrical and unsymmetrical ethers from aldehydes and ketones can be conveniently performed using Yb(OTf)3 as catalyst and triethylsilane as reducing agent in presence of alcohols. This methodology leads to the synthesis of ether derivatives with good yields. Notably, this process resulted a useful tool to protect alcohols as benzyl ether derivatives using differently substituted benzaldehydes as protecting agents under mild conditions. A plausible mechanism was also proposed. (Figure presented.).
Reductive Etherification via Anion-Binding Catalysis
Zhao, Chenfei,Sojdak, Christopher A.,Myint, Wazo,Seidel, Daniel
supporting information, p. 10224 - 10227 (2017/08/10)
Reductive condensations of alcohols with aldehydes/ketones to generate ethers are catalyzed by a readily accessible thiourea organocatalyst that operates in combination with HCl. 1,1,3,3-tetramethyldisiloxane serves as a convenient reducing reagent. This strategy is applicable to challenging substrate combinations and exhibits functional group tolerance. Competing reductive homocoupling of the carbonyl component is suppressed.
Photoredox Cross-Coupling: Ir/Ni Dual Catalysis for the Synthesis of Benzylic Ethers
Karakaya, Idris,Primer, David N.,Molander, Gary A.
supporting information, p. 3294 - 3297 (2015/07/15)
Single-electron transmetalation has emerged as an enabling paradigm for the cross-coupling of Csp3 hybridized organotrifluoroborates. Cross-coupling of α-alkoxymethyltrifluoroborates with aryl and heteroaryl bromides has been demonstrated by employing dual catalysis with a combination of an iridium photoredox catalyst and a Ni cross-coupling catalyst. The resulting method enables the alkoxymethylation of diverse (hetero)arenes under mild, room-temperature conditions. (Chemical Equation Presented).
Synthesis of ethers from carbonyl compounds by reductive etherification catalyzed by iron(III) and silyl chloride
Savela, Risto,Leino, Reko
, p. 1749 - 1760 (2015/06/16)
A simple iron- and silyl chloride catalyzed method for the preparation of symmetrical and nonsymmetrical ethers is presented. Various aldehydes and ketones were reductively etherified by using triethylsilane as a reducing agent in the presence of 2 mol% of iron(III) oxo acetate and 8 mol% of chloro(trimethyl)silane. The reactions can be carried out at ambient temperatures and pressures with ethyl acetate as the solvent.
Ferric perchlorate as an efficient and useful catalyst for the selective benzylation and methylation of alcohols with benzyl chloride and methyl iodide
Behbahani, Farahnaz K.,Heravi, Majid M.,Oskooie, Hossien A.
experimental part, p. 181 - 184 (2010/03/26)
A mild and efficient method was developed for selective benzylation and methylation of hydroxyl compounds in the presence of a catalytic amount of ferric perchlorate. We showed that ferric perchlorate was very effective in selectively promoting the benzylation and methylation of primary aliphatic and benzylic alcohols versus secondary aliphatic alcohols and phenolic hydroxy groups. Graphical abstract: [Figure not available: see fulltext.]
A highly efficient method for the reductive etherification of carbonyl compounds with triethylsilane and alkoxytrimethylsilane catalyzed by iron(III) chloride
Iwanami, Katsuyuki,Seo, Hana,Tobita, Yuki,Oriyama, Takeshi
, p. 183 - 186 (2007/10/03)
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.
Novel reactions of ethylene acetals with silyl-substituted nucleophiles. A mild and efficient procedure for the synthesis of homoallyl alkyl ethers and unsymmetrical dialkyl ethers
Suzuki, Takeshi,Oriyama, Takeshi
, p. 1263 - 1269 (2007/10/03)
Efficient one-pot synthesis of homoallyl alkyl ethers and dialkyl ethers was performed by the allylation and reduction of ethylene acetals with allyltrimethylsilane and t-butyldimethylsilane, respectively, in the presence of alkoxytrimethylsilane.
N-NITROSOHYDROXYLAMINES I. ACETOLYSIS AND ACID-CATALYZED HYDROLYSIS OF N,O-DIBENZYL-N-NITROSOHYDROXYLAMINES. REACTION WITH POTASSIUM t-BUTOXIDE
Kano, Kunio,Anselme, Jean-Pierre
, p. 10075 - 10086 (2007/10/02)
The major products of the hydrolysis of N,O-dibenzyl-N-nitrosohydroxylamines (3) are the denitrosated parent hydroxylamines (6); under more forcing conditions, products of the further hydrolysis of 6 are obtained.Acetolysis in acetic acid gives the benzyl acetates derived from both N- and O-substituents.With potassium tert-butoxide, the major path is abstraction of an O-benzyl hydrogen followed by fragmentation to the aldehyde and the benzyldiazotate ion.Possible mechanisms for the formation of the products are discussed.
Amidinoureas substituted in both the urea and amidino nitrogen positions
-
, (2008/06/13)
A method of inducing blood pressure reduction in humans and mammals by administering 2,6-disubstituted phenyl N-alkyl amidinoureas in which the phenyl ring is additionally substituted by a hydroxy, alkoxy, aralkoxy, alkenyloxy, alkynyloxy, acyloxy or halo acyloxy group and a novel class of amidinourea compounds having pharmaceutical uses, including blood pressure lowering activity.
