Selective Iron Catalyzed Synthesis of N-Alkylated Indolines and Indoles.

Autor: Wu J; Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) UMR 6226, 35000, Rennes, France., Tongdee S; Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) UMR 6226, 35000, Rennes, France., Cordier M; Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) UMR 6226, 35000, Rennes, France., Darcel C; Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) UMR 6226, 35000, Rennes, France.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2022 Sep 27; Vol. 28 (54), pp. e202201809. Date of Electronic Publication: 2022 Jul 22.
DOI: 10.1002/chem.202201809
Abstrakt: Whereas iron catalysts usually promote catalyzed C3-alkylation of indole derivatives via a 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). The one-pot, two-step strategy for the selective N-alkylation of indolines is completed by an oxidation to give the corresponding N-alkylated indoles in 31-90 % yields (15 examples). This unprecedented oxidation methodology involves an iron salt catalyst associated with (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) and a stoichiometric amount of t-BuOOH at room temperature.
(© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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