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铜催化的 1,8-二氨基萘保护的二硼酸对苯乙烯的硼化反应。

Copper-Catalyzed Borylation of Styrenes by 1,8-Diaminonaphthalene-Protected Diboronic Acid.

机构信息

Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601, Japan.

出版信息

Org Lett. 2023 Mar 31;25(12):2093-2097. doi: 10.1021/acs.orglett.3c00451. Epub 2023 Mar 22.

Abstract

We report a concise synthesis of 1,8-diaminonaphthalene-protected diboronic acid (B(dan)), which is a promising borylating agent. B(dan) is a bench-stable compound, and it could be utilized for Cu-catalyzed borylation of styrene derivatives. The reaction proceeded in a highly selective manner, and the products were isolated in up to 97% yields. Mechanistic studies revealed that a borate species would be a key intermediate for the borylation reaction.

摘要

我们报告了一种 1,8-二氨基萘保护的二硼酸(B(dan))的简洁合成方法,B(dan)是一种很有前途的硼化试剂。B(dan)是一种稳定的化合物,可以用于铜催化的苯乙烯衍生物的硼化反应。该反应具有高度的选择性,产物的收率高达 97%。机理研究表明,硼酸酯物种是硼化反应的关键中间体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e3c/10071482/ab46fcdfdb11/ol3c00451_0001.jpg

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