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Article Dans Une Revue Chemistry - A European Journal Année : 2022

Selective Iron Catalyzed Synthesis of N-alkylated Indolines and Indoles

Résumé

Whereas iron catalysts usually promote catalyzed C3-alkylation of indole derivatives via borrowing-hydrogen methodology using alcohols as the electrophilic partners, this contribution shows how to switch the selectivity towards N-alkylation. Thus starting from indoline derivatives, N-alkylation was efficiently performed using a tricarbonyl(cyclopentadienone) iron complex as the catalyst in trifluoroethanol in the presence of alcohols leading to the corresponding N-alkylated indoline derivatives in 31-99% yields (28 examples). It is then shown a one-pot, two-step strategy, for the selective N-alkylation of indolines then their oxidations, leading to the corresponding N-alkylated indoles in 31-90% yields (15 examples). This unprecedented oxidation methodology involves an iron salt catalyst associated to TEMPO and a stoichiometric amount of t- BuOOH at RT.

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Chimie
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Origine : Publication financée par une institution

Dates et versions

hal-03716511 , version 1 (22-09-2022)

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Jiajun Wu, Satawat Tongdee, Marie Cordier, Christophe Darcel. Selective Iron Catalyzed Synthesis of N-alkylated Indolines and Indoles. Chemistry - A European Journal, 2022, 28 (54), pp.e202201809. ⟨10.1002/chem.202201809⟩. ⟨hal-03716511⟩
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