Metal-free C(sp2)–H functionalization of azoles: K2CO3/I2-mediated oxidation, imination, and amination

The direct C2−H oxidation and imination of a wide variety of azoles was achieved by using a commercially available simple K2CO3/I2 reagent combination. The iodinated azole adduct, produced via the in situ generation of N-heterocyclic carbene, is the key intermediate for C2−H oxidation, imination, an...

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Veröffentlicht in:	Organic & biomolecular chemistry 2018, Vol.16 (23), p.4243-4260
Hauptverfasser:	Das, Ranajit, Banerjee, Mainak, Rai, Rakesh Kumar, Karri, Ramesh, Gouriprasanna Roy
Format:	Artikel
Sprache:	eng
Schlagworte:	Amination Aromatic compounds Azoles Heterocyclic compounds Oxidation Pharmacology Potassium carbonate Reagents Substrates
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creator	Das, Ranajit Banerjee, Mainak Rai, Rakesh Kumar Karri, Ramesh Gouriprasanna Roy
description	The direct C2−H oxidation and imination of a wide variety of azoles was achieved by using a commercially available simple K2CO3/I2 reagent combination. The iodinated azole adduct, produced via the in situ generation of N-heterocyclic carbene, is the key intermediate for C2−H oxidation, imination, and amination of azoles. Significantly, these reactions proceed under mild conditions with high to excellent yields, are scalable to large quantity and exhibit a broad substrate scope. Interestingly, this direct C2−H imination method allowed us to access various pharmacologically active N6-alkyl or N6-aryl substituted benzimidazoquinazolinone scaffolds through intramolecular C−H imination in a sequential one-pot reaction.
doi_str_mv	10.1039/c8ob00535d
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subjects	Amination Aromatic compounds Azoles Heterocyclic compounds Oxidation Pharmacology Potassium carbonate Reagents Substrates
title	Metal-free C(sp2)–H functionalization of azoles: K2CO3/I2-mediated oxidation, imination, and amination
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