Palladium-Catalyzed Oxidative Amination of α‑Olefins with Indoles

Herein we report the use of indoles, one of the most common nitrogen-containing heterocycles in FDA-approved drugs, as nucleophiles in the Pd-catalyzed aza-Wacker reaction. This N-functionalization of indoles is a Markovnikov selective olefin functionalization of simple alkenes using catalytic Pd(N...

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Veröffentlicht in:	Organic letters 2022-08, Vol.24 (31), p.5746-5750
Hauptverfasser:	Bhatt, Shreeja, Wang, Ya-Nong, Pham, Hoang T. P., Hull, Kami L.
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkenes Amination Catalysis Indoles Molecular Structure Oxidative Stress Palladium
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creator	Bhatt, Shreeja Wang, Ya-Nong Pham, Hoang T. P. Hull, Kami L.
description	Herein we report the use of indoles, one of the most common nitrogen-containing heterocycles in FDA-approved drugs, as nucleophiles in the Pd-catalyzed aza-Wacker reaction. This N-functionalization of indoles is a Markovnikov selective olefin functionalization of simple alkenes using catalytic Pd(NPhth)2(PhCN)2 and O2 as the terminal oxidant in the presence of catalytic Bu4NBr. Various substituted indoles and alkenes are found to participate; 21 examples are presented with yields ranging from 41 to 97% isolated yield. Additionally, lactams and oxazolidinones are shown to participate under the reaction conditions. Mechanistic investigations suggest that the phthalimide ligand and Bu4NBr additive slow undesired side reactions: indole decomposition and olefin isomerization, respectively.
doi_str_mv	10.1021/acs.orglett.2c02190
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subjects	Alkenes Amination Catalysis Indoles Molecular Structure Oxidative Stress Palladium
title	Palladium-Catalyzed Oxidative Amination of α‑Olefins with Indoles
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