Impact Factor:16.1
DOI number:10.1021/jacs.5c13420
Journal:J. Am. Chem. Soc
Abstract: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.
Indexed by:Journal paper
Discipline:Natural Science
Volume:147
Issue:43
Page Number:39721–39731
ISSN No.:0002-7863
Translation or Not:no
Date of Publication:2026-03-04
Included Journals:SCI
Links to published journals:https://pubs.acs.org/doi/10.1021/jacs.5c13420
Date of Publication:2026-03-04