羰基化
芳基
化学
催化作用
烷基
镍
催化循环
组合化学
迁移插入
电泳剂
有机化学
一氧化碳
作者
Troels Skrydstrup,Kim S. Mühlfenzl,Vitus J. Enemærke,Sahil Gahlawat,Peter I. Golbækdal,Nikoline Munksgaard-Ottosen,Karoline T. Neumann,Kathrin H. Hopmann,Per‐Ola Norrby,Charles S. Elmore
标识
DOI:10.1002/anie.202412247
摘要
Here we present an effective nickel‐catalyzed carbonylative cross‐coupling for direct access to alkyl aryl ketones from readily accessible redox‐activated tetrachlorophthalimide esters and aryl boronic acids. The methodology, which is run employing only 2.5 equivalents of CO and simple Ni(II) salts as the metal source, exhibits a broad substrate scope under mild condition. Furthermore, this carbonylation chemistry provides an easy switch between isotopologues for stable (13CO) and radioactive (14CO) isotope labeling, allowing its adaptation to the late‐stage isotope labeling of pharmaceutically relevant compounds. Based on DFT calculations as well as experimental evidence, a catalytic cycle is proposed involving a carbon‐centered radical formed via nickel(I)‐induced outer‐sphere decarboxylative fragmentation of the redox‐active ester.
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