54852-64-1Relevant academic research and scientific papers
Synthesis of Benzyl Alkyl Ethers by Intermolecular Dehydration of Benzyl Alcohol with Aliphatic Alcohols under the Effect of Copper Containing Catalysts
Bayguzina,Gimaletdinova,Khusnutdinov
, p. 1148 - 1155 (2018/10/24)
Synthesis of benzyl alkyl ethers was performed in high yields by intermolecular dehydration of benzyl and primary, secondary, tertiary alcohols under the effect of copper containing catalysts. The formation of benzyl alkyl ethers occurs with participation of benzyl cation.
1-Butyl-3-methylimidazol-2-ylidene Borane: A Readily Available, Liquid N-Heterocyclic Carbene Borane Reagent
Bolt, Daniel A.,Curran, Dennis P.
, p. 13746 - 13750 (2017/12/26)
1-Butyl-3-methylimidazol-2-ylidene borane has been synthesized directly from two inexpensive commercial reagents: 1-butyl-3-methylimidazolium bromide and sodium borohydride. This NHC-borane reagent is a stable, free-flowing liquid that shows promise for use in radical, ionic, and metal-catalyzed reactions.
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.
Visible-light-promoted conversion of alkyl benzyl ether to alkyl ester or alcohol via O-α-sp3 C-H cleavage
Lu, Ping,Hou, Tianyuan,Gu, Xiangyong,Li, Pixu
supporting information, p. 1954 - 1957 (2015/04/27)
A mild and high-yielding visible-light-promoted conversion of alkyl benzyl ethers to the alkyl esters or alkyl alcohols was developed. Mechanistic studies provided evidence for a radical chain reaction involving the homolytic cleavage of O-α-sp3 C-H bonds in the substrate as one of the propagation steps. We propose that α-bromoethers are key intermediates in the transformation.
Benzylation of arenes with benzyl ethers promoted by the in situ prepared superacid BF3-H2O
Li, Yu,Xiong, Yan,Li, Xueming,Ling, Xuege,Huang, Ruofeng,Zhang, Xiaohui,Yang, Jianchun
supporting information, p. 2976 - 2981 (2014/06/10)
An efficient and environmentally friendly benzylation of arenes with benzyl ethers as benzyl donors using BF3-Et2O to generate in situ the superacid BF3-H2O as an efficient promotor has been described. A wide variety of functional groups have been investigated and found to be compatible to give the desired diarylmethanes in yields of up to 99%. The crucial role of the moisture content in this transformation has been demonstrated by detailed investigations. This journal is the Partner Organisations 2014.
Disulfides and boryl sulfides serve as both initiators and precatalysts in radical reductions of halides by an N-heterocyclic carbene×Borane
Pan, Xiangcheng,Lalevee, Jacques,Lacote, Emmanuel,Curran, Dennis P.
, p. 3522 - 3526 (2014/01/06)
Diphenyl disulfide (PhSSPh), a typical boryl monosulfide (diiPr-Imd-BH 2SPh) and a typical boryl bis-sulfide [diMe-Imd-BH(SPh)2] all serve as both initiators and precatalysts in the reduction of alkyl and aryl halides by readily available 1,3-dimethylimidazol-2-ylidene×borane (diMe-Imd-BH3). The reactions are suggested to occur by a polarity reverse catalysis mechanism where in situ generated thiophenol is the active catalyst. Copyright
Mild and efficient capture and functionalisation of CO2 using silver(i) oxide and application to 13C-labelled dialkyl carbonates
Tunbridge, Gemma A.,Baruchello, Riccardo,Caggiano, Lorenzo
, p. 4613 - 4621 (2013/05/08)
A high yielding three-component reaction between β-iodo ethylamine derivatives, MeOH and gaseous CO2 at ambient temperatures and pressures is reported using silver(i) oxide. Unfunctionalised alkyl iodides were also found to be effective in this transformation and their optimisation is also described. To highlight the ease and control with which gaseous CO 2 can be captured and functionalised under mild conditions, the reaction was performed using 13C-enriched CO2 to afford specifically 13C-carbonyl-labelled dialkyl carbonates with exquisite control of the isotopic purity in good yields and without the need for specialised equipment.
A novel method for synthesis of benzyl alkyl ethers using Vanadium-based metal complex catalysts
Khusnutdinov,Bayguzina,Gallyamova,Dzhemilev
, p. 261 - 266 (2012/10/29)
A novel method has been developed for the synthesis of benzyl alkyl ethers in 25-85% yields via the reaction of toluene with alcohols in a CCl4 medium catalyzed by Et3N-activated VO(acac)2.
Polarity reversal catalysis in radical reductions of halides by N-heterocyclic carbene boranes
Pan, Xiangcheng,Lacote, Emmanuel,Lalevee, Jacques,Curran, Dennis P.
supporting information; experimental part, p. 5669 - 5674 (2012/06/04)
Otherwise sluggish or completely ineffective radical reductions of alkyl and aryl halides by N-heterocyclic carbene boranes (NHC-boranes) are catalyzed by thiols. Reductions and reductive cyclizations with readily available 1,3-dimethylimidazol-2-ylidene borane and a water-soluble triazole relative are catalyzed by thiophenol and tert-dodecanethiol [C9H 19C(CH3)2SH]. Rate constants for reaction of the phenylthiyl (PhS?) radical with two NHC-boranes have been measured to be ～108 M-1 s-1 by laser flash photolysis experiments. An analysis of the available evidence suggests the operation of polarity reversal catalysis.
Triflic acid catalyzed reductive coupling reactions of carbonyl compounds with O-, S-, and N-nucleophiles
Gellert, Beate A.,Kahlcke, Nils,Feurer, Markus,Roth, Stefanie
supporting information; experimental part, p. 12203 - 12209 (2011/11/07)
Highly efficient metal-free reductive coupling reactions of aldehydes and ketones with a range of nucleophiles in the presence of triflic acid (1-5 mol %) as the catalyst are presented. The reactions can be performed at ambient temperature without exclusion of moisture or air. A range of symmetrical and unsymmetrical ethers were obtained by this method in high yields and short reaction times. For the first time, the influence of additional functionalization has been studied. Furthermore, the formation of thioethers from ketones (by addition of unmodified thiols) and of sulfonamides from either aldehydes or ketones has been achieved under catalytic conditions.
