硼酸化
化学
邻苯二甲酰亚胺
酰胺
羧酸
反应性(心理学)
硼
催化作用
有机化学
组合化学
光化学
芳基
医学
病理
替代医学
烷基
作者
Alexander Fawcett,Johan A. Pradeilles,Yahui Wang,Tatsuya Mutsuga,Eddie L. Myers,Varinder K. Aggarwal
出处
期刊:Science
[American Association for the Advancement of Science (AAAS)]
日期:2017-07-20
卷期号:357 (6348): 283-286
被引量:580
标识
DOI:10.1126/science.aan3679
摘要
The conversion of widely available carboxylic acids into versatile boronic esters would be highly enabling for synthesis. We found that this transformation can be effected by illuminating the N-hydroxyphthalimide ester derivative of the carboxylic acid under visible light at room temperature in the presence of the diboron reagent bis(catecholato)diboron. A simple workup allows isolation of the pinacol boronic ester. Experimental evidence suggests that boryl radical intermediates are involved in the process. The methodology is illustrated by the transformation of primary, secondary, and tertiary alkyl carboxylic acids as well as a diverse range of natural-product carboxylic acids, thereby demonstrating its broad utility and functional group tolerance.
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