Pd0/PR3 催化的烟碱和异烟酸衍生物的芳基化反应。
Pd0/PR3-catalyzed arylation of nicotinic and isonicotinic acid derivatives.
机构信息
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
出版信息
Angew Chem Int Ed Engl. 2010 Feb 8;49(7):1275-7. doi: 10.1002/anie.200906104.
Abstract
The first example of C-H functionalizations of pyridine rings at the 3- and 4-positions is developed using Pd(0)/PR/ArBr. This reaction provides a powerful method for the preparation of structurally diverse nicotinic and isonicotinic acids that are of tremendous importance in drug discovery.
摘要
首次开发了使用 Pd(0)/PR/ArBr 实现吡啶环 3 位和 4 位 C-H 官能化的方法。该反应为制备结构多样的烟碱酸和异烟酸提供了一种强大的方法，这些酸在药物发现中具有重要意义。
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2
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