42100-74-3Relevant academic research and scientific papers
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.
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%.
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.
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.
Borderline mechanisms involving ion-molecule pairs for the nucleophilic substitution reactions of benzhydrol and its derivatives. Facile formation and cleavage of diphenylmethyl ethers for the protection of hydroxyl groups
Paredes, Rodrigo,Perez, Ruby L.
, p. 2037 - 2038 (2007/10/03)
Nucleophilic substitution reactions of benzhydrol and its derivatives, in refluxing benzene in the presence of para-toluenesulfonic acid, took different routes depending on whether paratoluenesulfonic acid was used in excess or in catalytic amounts. In the first case the reactions took place via benzhydryl carbocations and in the second case they proceeded via intimate ion-molecule pairs. On the basis of this study, facile methods for introduction and removal of CHPh2 as a protective group of alcohols are presented.
