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Aerobic C(sp2)–H Hydroxylations of 2-Aryloxazolines: Fast Access to Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores

Authors :
Göbel, Dominik
Clamor, Nils
Lork, Enno
Nachtsheim, Boris J.
Source :
Organic Letters; July 2019, Vol. 21 Issue: 14 p5373-5377, 5p
Publication Year :
2019

Abstract

The direct hydroxylation of 2-aryloxazolines via a deprotonative magnesiation using TMPMgCl·LiCl and subsequent oxidation with molecular oxygen or air as a green oxidant is reported. This method proceeds under mild conditions at room temperature with high regioselectivity and chemoselectivity. The obtained phenols exhibit tunable luminescence properties, induced by excited-state intramolecular proton transfer. This method opens a new opportunity for the sustainable synthesis of luminescent organic molecules.

Details

Language :
English
ISSN :
15237060 and 15237052
Volume :
21
Issue :
14
Database :
Supplemental Index
Journal :
Organic Letters
Publication Type :
Periodical
Accession number :
ejs50176168
Full Text :
https://doi.org/10.1021/acs.orglett.9b01350