42113-39-3Relevant academic research and scientific papers
Direct conversion of silyl ethers or tetrahydropyranyl ethers into the corresponding diphenylmethyl ethers
Suzuki,Kobayashi,Noda,Oriyama
, p. 2761 - 2766 (2001)
Direct conversion of alcohol silyl ethers into the corresponding diphenylmethyl (DPM) ethers can be easily performed by the reaction with diphenylmethyl formate in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate. By the additional use of triethylsilane, tetrahydropyranyl ethers can be also converted into the corresponding DPM ethers.
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.
Direct and efficient synthesis of unsymmetrical ethers from alcohols catalyzed by Fe(HSO4)3 under solvent-free conditions
Moghadam, Bashir Nazari,Akhlaghinia, Batool,Rezazadeh, Soodabeh
, p. 1487 - 1501 (2016/04/26)
Highly efficient Fe(HSO4)3 catalyzed etherification of primary, secondary and tertiary benzylic alcohols with primary and secondary aliphatic alcohols is reported. The reaction affords unsymmetrical benzyl ethers in good to excellent yields under solvent-free conditions.
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
, 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.
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.
PdCl2, a useful catalyst for protection of alcohols as diphenylmethyl (DPM) ethers
Bikard, Yann,Weibel, Jean-Marc,Sirlin, Claude,Dupuis, Luc,Loeffler, Jean-Philippe,Pale, Patrick
, p. 8895 - 8899 (2008/03/14)
Primary, secondary, benzylic and allylic alcohols are efficiently converted to the corresponding diphenylmethyl ethers in the presence of catalytic amounts of PdCl2.
