26059-49-4Relevant academic research and scientific papers
Method for synthesizing ether by catalyzing alcohol through trimethyl halosilane
-
Paragraph 0075-0078, (2020/12/29)
The invention discloses a method for synthesizing ether by catalyzing alcohol through trimethyl halosilane. According to the method, under the conditions of air or nitrogen atmosphere, no solvent andno transition metal catalyst, an alcohol compound is directly used as a raw material, trimethyl halosilane is used as a catalyst, and symmetric or asymmetric ether is synthesized through one-step selective dehydration reaction. According to the method, the use of strong acid, strong base and organic primary halides with high toxicity, instability and higher price is avoided, the synthesis steps are shortened, the synthesis efficiency is improved, the reaction has good selectivity, and a target ether product can be obtained preferentially.
Benzyl C–O and C–N Bond Construction via C–C Bond Dissociation of Oxime Ester under Visible Light Irradiation
Fan, Xiuwei,Lei, Tao,Liu, Zan,Yang, Xiu-Long,Cheng, Yuan-Yuan,Liang, Ge,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
, p. 1551 - 1558 (2019/09/09)
A photoredox benzyl activation was developed via formidable C(sp3)–C(sp3) bond dissociation of 1-aryl acetone oxime esters, which were easily prepared from benzyl ketones. Further coupling with O- and N- nucleophiles successfully forged important benzyl ether and amines derivatives in one pot. In this process, different substitutions on oxime esters were found compatible and various primary and secondary alcohols and amines, as well as amides showed good performance as nucleophiles. Mechanistic studies by control experiments, electrochemical measurements and in-situ NMR spectra proposed a N–O bond interruption/C–C bond fragmentation/oxidation sequence to provide the key cation intermediate for the next electrophilic SN process. The features of mild condition, short reaction time and broad substrate scope made this new strategy much promising in the transformation of benzyl compounds, which might be valuable in last-stage functionalizations.
Development of dipyridine-based coordinative polymers for reusable heterogeneous catalysts
Chang, Hsiang-Chun,Li, Jia-Qi,Lin, Ching-Kai,Hsu, Yu-Jung,Tu, Tsung-Han,Hsieh, Yi-Liang,Hsu, Hsiu-Hao,Lee, Gene-Hsiang,Liu, Yi-Hung,Peng, Chi-How
, p. 1119 - 1133 (2019/08/01)
Poly(di(pyridin-2-yl)methyl acrylate) (PDPyMA), which was obtained by the free radical polymerization of designed coordinative monomer of di(pyridin-2-yl)methyl acrylate, is able to coordinate with various metal ions to form heterogeneous catalysts for diverse catalytic reactions. The Pd and Cu complexes supported by PDPyMA were developed for the heterogeneous Suzuki-Miyaura reaction and Friedel-Crafts alkylation, respectively. The PDPyMA-based catalysts showed no significant decline of reactivity after five times recycling. However, the hydrolysis of the PDPyMA backbone under alkaline conditions limited the catalytic efficiency of this heterogeneous catalyst so that the coordinative monomer was redesigned as 1,1-di(pyridine-2-yl)-2-(4-vinylphenyl)ethan-1-ol and then 2,2′-(1-methoxy-2-(4-vinylphenyl)ethane-1,1-diyl)dipyridine (MVPhDPy). With copolymerization of N-isopropyl acrylamide (NIPAM), the efficiency of polymer-based heterogeneous catalysts could be further raised, demonstrated by the increased turn over number in the Suzuki-Miyaura reaction, which approached 5,260 by using the catalyst formed from poly(MVPhDPy-co-NIPAM) and Pd(OAc)2. poly(MVPhDPy-co-NIPAM) copolymer, therefore, could be a versatile platform to support different metal ions for various heterogeneous catalytic reactions.
Practical preparation of diphenylmethyl ethers from 2-diphenylmethoxypyridine using catalytic iron(III) chloride
Tran, Van Hieu,La, Minh Thanh,Kim, Hee-Kwon
, p. 6221 - 6228 (2019/07/04)
A novel facile synthetic method for producing diphenylmethyl (DPM) ethers from 2-diphenylmethoxypyridine was developed. A variety of DPM ethers was successfully achieved with high yield via treatment of alcohols with 2-diphenylmethoxypyridine in the presence of catalytic FeCl3. The procedure is a practical and efficient synthetic procedure to protect various alcohols, and it can be applied to prepare bioactive compounds.
B(C6F5)3 catalyzed direct nucleophilic substitution of benzylic alcohols: an effective method of constructing C-O, C-S and C-C bonds from benzylic alcohols
Meng, Shan-Shui,Wang, Qian,Huang, Gong-Bin,Lin, Li-Rong,Zhao, Jun-Ling,Chan, Albert S. C.
, p. 30946 - 30949 (2018/09/13)
An efficient and general method of nucleophilic substitution of benzylic alcohols catalyzed by non-metallic Lewis acid B(C6F5)3 was developed. The reaction could be carried out under mild conditions and more than 35 exampl
Method for catalyzing etherification of benzyl alcohol compounds
-
Paragraph 0029; 0030; 0031, (2018/11/22)
The invention belongs to the field of organic synthesis and discloses a method for catalyzing the etherification of benzyl alcohol compounds. The benzyl alcohol compounds are mixed with an alcohol compound A, and a solvent and tripentafluorophenylborane s
Formation of DPM ethers using O-diphenylmethyl trichloroacetimidate under thermal conditions
Howard, Kyle T.,Duffy, Brian C.,Linaburg, Matthew R.,Chisholm, John D.
supporting information, p. 1623 - 1628 (2016/02/09)
Alcohols are effectively converted to their corresponding diphenylmethyl (DPM) ethers by reaction with O-diphenylmethyl trichloroacetimidate in refluxing toluene without the requirement of a catalyst or other additives. A number of acid and base sensitive substrates were protected in excellent yield using this new method without disturbing the pre-existing functionality present in these molecules. This reaction is the first example of the formation of an ether from stoichiometric amounts of a trichloroacetimidate and an alcohol without the addition of a Br?nsted or Lewis acid catalyst.
Organohalide-catalyzed dehydrative O-alkylation between alcohols: A facile etherification method for aliphatic ether synthesis
Xu, Qing,Xie, Huamei,Chen, Pingliang,Yu, Lei,Chen, Jianhui,Hu, Xingen
supporting information, p. 2774 - 2779 (2015/05/27)
Organohalides are found to be effective catalysts for dehydrative O-alkylation reactions between alcohols, providing selective, practical, green, and easily scalable homo- and cross-etherification methods for the preparation of useful symmetrical and unsymmetrical aliphatic ethers from the readily available alcohols. Mechanistic studies revealed that organohalides are regenerated as reactive intermediates and recycled to catalyze the reactions.
Boron Trifluoride?Diethyl Ether-Catalyzed Etherification of Alcohols: A Metal-Free Pathway to Diphenylmethyl Ethers
Li, Jiaqiang,Zhang, Xiaohui,Shen, Hang,Liu, Qing,Pan, Jing,Hu, Wen,Xiong, Yan,Chen, Changguo
supporting information, p. 3115 - 3120 (2015/11/03)
A novel boron trifluoride?diethyl ether (BF3?OEt2)-catalyzed etherification procedure has been developed in which primary and secondary alcohols are easily converted into diphenylmethyl ethers with yields of up to 99%.
Gold(I)-catalyzed synthesis of unsymmetrical ethers using alcohols as alkylating reagents
Liu, Yongxiang,Wang, Xiaoyu,Wang, Yanshi,Du, Chuan,Shi, Hui,Jin, Shengfei,Jiang, Chongguo,Xiao, Jianyong,Cheng, Maosheng
, p. 1029 - 1036 (2015/03/30)
A microwave-irradiated alcohol-protecting strategy based on gold catalysis utilizing benzyl alcohol, tert-butyl alcohol and triphenylmethanol as alkylating reagents has been developed. This protecting strategy has wide functional group tolerance with satisfactory yields for the majority of the selected alcohols. The mechanism of this transformation was probed with oxygen-18 isotope labelled alcohols assisted by GC-MS techniques and chemical kinetic experiments. This strategy provides an efficient, straightforward and alternative approach to the preparation of benzyl, tert-butyl and trityl ethers in organic synthesis.
