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De Novo” Construction of Planar-Chiral Ferrocenes via Palladium/Chiral Norbornene Cooperative Catalysis

发布时间：2026-06-21
点击次数：

影响因子：16.1
DOI码：10.1021/jacs.5c13420
发表刊物：J. Am. Chem. Soc
摘要：Transition-metal-catalyzed asymmetric C–H functionalization has emerged as a powerful strategy for constructing planar-chiral ferrocenes (PCFs). However, current methods typically require preinstallation of a directing group (DG) and are usually limited to monofunctionalization. Herein, we report a “de novo” construction of PCFs via Pd/NBE* cooperative catalysis, employing a unique bulky (C1,C4)-bridgehead-modified chiral norbornene as the cocatalyst as well as the only chiral source. This approach enables the formation of two new chemical bonds in a single step from simple iodoferrocenes. A series of planar-chiral isoquinolone-fused ferrocenes are quickly obtained with up to >99% ee. Mechanistic studies reveal that the ortho-C–H activation step serves as the enantio-determining step, while the reductive elimination is not only the rate-determining step but also plays a pivotal role in further enhancing the enantioselectivity. The synthetic utility is highlighted by diverse transformations of products and the development of a powerful NAD(P)H coenzyme for biomimetic asymmetric hydrogenation of olefins.
论文类型：期刊论文
学科门类：理学
卷号：147
期号：43
页面范围：39721–39731
ISSN号：0002-7863
是否译文：否
发表时间：2026-03-04
收录刊物：SCI
发布期刊链接：https://pubs.acs.org/doi/10.1021/jacs.5c13420