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Rhodium(III)‐Catalyzed ortho ‐Heteroarylation of Phenols through Internal Oxidative CH Activation: Rapid Screening of Single‐Molecular White‐Light‐Emitting Materials
Author(s) -
Li Bijin,
Lan Jingbo,
Wu Di,
You Jingsong
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201507272
Subject(s) - triphenylamine , chemistry , catalysis , rhodium , intramolecular force , quantum yield , photochemistry , phenol , phenols , excited state , iridium , oxidative coupling of methane , organic chemistry , fluorescence , physics , quantum mechanics , nuclear physics
Reported herein is the first example of a transition‐metal‐catalyzed internal oxidative CH/CH cross‐coupling between two (hetero)arenes through a traceless oxidation directing strategy. Without the requirement of an external metal oxidant, a wide range of phenols, including phenol‐containing natural products, can undergo the coupling with azoles to assemble a large library of highly functionalized 2‐(2‐hydroxyphenyl)azoles. The route provides an opportunity to rapidly screen white‐light‐emitting materials. As illustrative examples, two bis(triphenylamine)‐bearing 2‐(2‐hydroxyphenyl)oxazoles, which are difficult to access otherwise, exhibit bright white‐light emission, high quantum yield, and thermal stability. Also presented is the first example of the white‐light emission, in a single excited‐state intramolecular proton transfer system, of 2‐(2‐hydroxyphenyl)azoles, thus highlighting the charm of CH activation in the discovery of new organic optoelectronic materials.