Regiospecificity in Ligand-Free Pd-Catalyzed C–H Arylation of Indoles: LiHMDS as Base and Transient Directing Group - Université de Montpellier Accéder directement au contenu
Article Dans Une Revue ACS Catalysis Année : 2020

Regiospecificity in Ligand-Free Pd-Catalyzed C–H Arylation of Indoles: LiHMDS as Base and Transient Directing Group

Résumé

A highly efficient catalyst-base pair for the C-H arylation of free (NH)-indoles in the C-3 position is reported. Ligand-free palladium acetate coupled with lithium hexamethyldisilazide (LiHMDS) catalyzed the regiospecific, i.e. 100% regioselective, C-3 arylation of indoles with high turnover numbers. This catalytic system has been successfully applied to a wide range of substrates including various functional aryl halides and indolic cores. The unique role of LiHMDS as both a base and unexpected transient directing group has been revealed experimentally and elucidated computationally, in line with a Heck-type insertion-elimination mechanism.

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Chimie
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Dates et versions

hal-02493979 , version 1 (18-05-2020)

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Yorck Mohr, Marc Renom-Carrasco, Clément Demarcy, Elsje Alessandra Quadrelli, Clément Camp, et al.. Regiospecificity in Ligand-Free Pd-Catalyzed C–H Arylation of Indoles: LiHMDS as Base and Transient Directing Group. ACS Catalysis, 2020, 10 (4), pp.2713-2719. ⟨10.1021/acscatal.9b04864⟩. ⟨hal-02493979⟩
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