Aryl Boronic Acid Catalysed Dehydrative Substitution of Benzylic Alcohols for C-O Bond Formation

被引：41
|
作者：
Estopina-Duran, Susana [1 ]
Donnelly, Liam J. [1 ]
Mclean, Euan B. [1 ]
Hockin, Bryony M. [1 ]
Slawin, Alexandra M. Z. [1 ]
Taylor, James E. [1 ,2 ]
机构：
[1] Univ St Andrews, EaStCHEM, Sch Chem, St Andrews KY16 9ST, Fife, Scotland
[2] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 15期
基金：
英国工程与自然科学研究理事会;
关键词：
alcohols; boronic acids; etherification; homogeneous catalysis; substitution; FRIEDEL-CRAFTS REACTIONS; PI-ACTIVATED ALCOHOLS; NUCLEOPHILIC-SUBSTITUTION; ALLYLIC ALCOHOLS; MILD; MITSUNOBU; DERIVATIVES; AMINATION; TRIFLATE; AMINES;
D O I：
10.1002/chem.201806057
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A combination of pentafluorophenylboronic acid and oxalic acid catalyses the dehydrative substitution of benzylic alcohols with a second alcohol to form new C-O bonds. This method has been applied to the intermolecular substitution of benzylic alcohols to form symmetrical ethers, intramolecular cyclisations of diols to form aryl-substituted tetrahydrofuran and tetrahydropyran derivatives, and intermolecular crossed-etherification reactions between two different alcohols. Mechanistic control experiments have identified a potential catalytic intermediate formed between the aryl boronic acid and oxalic acid.
引用
收藏
页码：3950 / 3956
页数：7
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