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可见光照介导的对乙烯基硼酸酯的脱羧基自由基加成反应:快速得到 γ-氨基硼酸酯。

Visible-Light-Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ-Amino Boronic Esters.

机构信息

School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.

出版信息

Angew Chem Int Ed Engl. 2018 Feb 19;57(8):2155-2159. doi: 10.1002/anie.201712186. Epub 2018 Jan 26.

Abstract

The synthesis of alkyl boronic esters by direct decarboxylative radical addition of carboxylic acids to vinyl boronic esters is described. The reaction proceeds under mild photoredox catalysis and involves an unprecedented single-electron reduction of an α-boryl radical intermediate to the corresponding anion. The reaction is amenable to a diverse range of substrates, including α-amino, α-oxy, and alkyl carboxylic acids, thus providing a novel method to rapidly access boron-containing molecules of potential biological importance.

摘要

本文描述了通过羧酸对乙烯基硼酸酯的直接脱羧基自由基加成来合成烷基硼酸酯的方法。该反应在温和的光氧化还原催化条件下进行,涉及α-硼自由基中间体的前所未有的单电子还原为相应的阴离子。该反应适用于多种底物,包括α-氨基、α-氧基和烷基羧酸,因此为快速获得具有潜在生物学重要性的含硼分子提供了一种新方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6b37/5838549/0a82d521795c/ANIE-57-2155-g001.jpg

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