使用路易斯碱活化的硼酸酯亲核试剂对醛进行化学选择性苄基化反应。
Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles.
作者信息
Hollerbach Michael R, Barker Timothy J
机构信息
Department of Chemistry and Biochemistry, College of Charleston, 66 George St., Charleston, South Carolina 29424 United States.
出版信息
Organometallics. 2018 May 14;37(9):1425-1427. doi: 10.1021/acs.organomet.8b00085. Epub 2018 Apr 27.
Abstract
A benzylation of aldehydes using primary and secondary benzylboronic acid pinacol esters is reported. Activation of the boronic ester with -butyllithium rendered it nucleophilic toward aldehydes. The activated nucleophile chemoselectively transfers the benzyl group over the -butyl group, providing excellent yields of the benzylated products. B NMR experiments were performed to study the mechnism of this transformation.
摘要
报道了使用伯苄基硼酸频哪醇酯和仲苄基硼酸频哪醇酯对醛进行苄基化反应。用正丁基锂活化硼酸酯使其对醛具有亲核性。活化后的亲核试剂在化学选择性上优先将苄基转移至醛上，而非正丁基，从而得到高产率的苄基化产物。进行了硼核磁共振实验以研究该转化反应的机理。
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