Double cobalt-catalyzed atroposelective C–H activation: One-step synthesis of atropisomeric indoles bearing vicinal C–C and C–N diaxes - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chem Catalysis Année : 2023

Double cobalt-catalyzed atroposelective C–H activation: One-step synthesis of atropisomeric indoles bearing vicinal C–C and C–N diaxes

Résumé

Expanding the borders of asymmetric synthesis by designing original chiral molecules and sustainable strategies to synthesize them holds great promise not only for the pharmaceutical industry but also for material science and agrochemistry. In particular, straightforward, one-step synthesis of enantiopure scaffolds featuring two proximal chiral axes presents a great scientific challenge. Herein, unique asymmetric C-H activation reaction has been used to achieve the first intermolecular direct arylation-type reaction, affording indoles bearing simultaneously C2-atropisomeric Ar-Ar' axis together with C-N axial chirality. Remarkably, the desired reactivity could be achieved using a chiral cobalt complex as a sustainable and cheap catalyst, thus delivering the expected multiatropisomeric compounds in high yields and excellent diastereoselectivities and enantioselectivities. In addition, detailed mechanistic studies provide fundamental comprehension of this unique transformation.

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Chimie
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jeudi 25 juillet 2024
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jeudi 25 juillet 2024
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Dates et versions

hal-04418400 , version 1 (25-01-2024)

Identifiants

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Amandine Luc, João C.A. Oliveira, Philipp Boos, Nicolas Jacob, Lutz Ackermann, et al.. Double cobalt-catalyzed atroposelective C–H activation: One-step synthesis of atropisomeric indoles bearing vicinal C–C and C–N diaxes. Chem Catalysis, 2023, 3 (10), pp.100765. ⟨10.1016/j.checat.2023.100765⟩. ⟨hal-04418400⟩
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