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通过鏻盐实现钯催化吡啶衍生物的亲电官能化反应

Palladium-Catalyzed Electrophilic Functionalization of Pyridine Derivatives through Phosphonium Salts.

作者信息

Che Yuan-Yuan, Yue Yanni, Lin Ling-Zhi, Pei Bingbing, Deng Xuezu, Feng Chao

机构信息

Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing, 211816, P. R. China.

出版信息

Angew Chem Int Ed Engl. 2020 Sep 14;59(38):16414-16419. doi: 10.1002/anie.202006724. Epub 2020 Jul 15.

Abstract

Herein, we report a highly efficient and practical method for pyridine-derived heterobiaryl synthesis through palladium-catalyzed electrophilic functionalization of easily available pyridine-derived quaternary phosphonium salts. The nice generality of this reaction was goes beyond arylation, enabling facile incorporation of diverse carbon-based fragments, including alkenyl, alkynyl, and also allyl fragments, onto the pyridine core. Notably, the silver salt additive is revealed to be of vital importance for the success of this transformation and its pivotal role as transmetallation mediator, which guarantees a smooth transfer of pyridyl group to palladium intermediate, is also described.

摘要

在此,我们报道了一种高效实用的方法,通过钯催化易于获得的吡啶衍生季鏻盐的亲电官能化反应来合成吡啶衍生的杂联芳基。该反应具有良好的通用性,不仅限于芳基化反应,还能使包括烯基、炔基以及烯丙基片段在内的各种碳基片段轻松引入吡啶核心。值得注意的是,银盐添加剂被证明对该转化反应的成功至关重要,并且还描述了其作为转金属化介质的关键作用,该作用确保了吡啶基顺利转移至钯中间体。

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