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通过三氟化硼掩蔽策略实现二硼(4)的去对称化:不对称二硼物种的实用合成

Desymmetrization of Diboron(4) by a Trifluorination B-Masking Strategy: Practical Synthesis of Unsymmetrical Diboron Species.

作者信息

Eghbarieh Nadim, Masarwa Ahmad

机构信息

Institute of Chemistry, The Center for Nanoscience and Nanotechnology, and Casali Center for Applied Chemistry, The Hebrew University of Jerusalem, Jerusalem 9190401, Israel.

出版信息

J Org Chem. 2024 Aug 16;89(16):11753-11760. doi: 10.1021/acs.joc.4c00715. Epub 2024 Jul 31.

Abstract

Herein, we report a straightforward practical and simple method for efficiently synthesizing a BF-containing unsymmetrical diboron salt. This method involves the direct desymmetrization of commercially available diboron(4). This desymmetrization is based on a selective B-masking strategy via nucleophilic trifluorination, providing the elusive diborons bearing a trifluoroborate group. The synthetic utility of these salts is demonstrated through various examples of (sequential) B-ligand interconversions, enabling the synthesis of unsymmetrical diboron derivatives. These products, which serve as valuable building blocks, are obtained in gram-scale and high yields.

摘要

在此,我们报道了一种直接、实用且简单的方法,用于高效合成含硼的不对称二硼盐。该方法涉及市售二硼化合物(4)的直接去对称化。这种去对称化基于通过亲核三氟氟化的选择性硼掩蔽策略,得到了带有三氟硼酸盐基团的难以捉摸的二硼化合物。通过(连续的)硼-配体相互转化的各种实例证明了这些盐的合成效用,从而能够合成不对称二硼衍生物。这些作为有价值的结构单元的产物以克级规模和高收率获得。

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