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Li B, Lan J, Wu D, et al. Rhodium(III)-Catalyzed ortho-Heteroarylation of Phenols through Internal Oxidative C-H Activation: Rapid Screening of Single-Molecular White-Light-Emitting Materials. Angew Chem Int Ed Engl. 2015;54(47):14008-12doi: 10.1002/anie.201507272.
Li, B., Lan, J., Wu, D., & You, J. (2015). Rhodium(III)-Catalyzed ortho-Heteroarylation of Phenols through Internal Oxidative C-H Activation: Rapid Screening of Single-Molecular White-Light-Emitting Materials. Angewandte Chemie (International ed. in English), 54(47), 14008-12. https://doi.org/10.1002/anie.201507272
Li, Bijin, et al. "Rhodium(III)-Catalyzed ortho-Heteroarylation of Phenols through Internal Oxidative C-H Activation: Rapid Screening of Single-Molecular White-Light-Emitting Materials." Angewandte Chemie (International ed. in English) vol. 54,47 (2015): 14008-12. doi: https://doi.org/10.1002/anie.201507272
Li B, Lan J, Wu D, You J. Rhodium(III)-Catalyzed ortho-Heteroarylation of Phenols through Internal Oxidative C-H Activation: Rapid Screening of Single-Molecular White-Light-Emitting Materials. Angew Chem Int Ed Engl. 2015 Nov 16;54(47):14008-12. doi: 10.1002/anie.201507272. Epub 2015 Sep 25. PMID: 26403373.
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Angew Chem Int Ed Engl. 2015 Nov 16;54(47):14008-12. doi: 10.1002/anie.201507272. Epub 2015 Sep 25.

Rhodium(III)-Catalyzed ortho-Heteroarylation of Phenols through Internal Oxidative C-H Activation: Rapid Screening of Single-Molecular White-Light-Emitting Materials.

Angewandte Chemie (International ed. in English)

Bijin Li, Jingbo Lan, Di Wu, Jingsong You

Affiliations

  1. Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (PR China).
  2. Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (PR China). [email protected].
  3. Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (PR China). [email protected].

PMID: 26403373 DOI: 10.1002/anie.201507272

Abstract

Reported herein is the first example of a transition-metal-catalyzed internal oxidative C-H/C-H 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 C-H activation in the discovery of new organic optoelectronic materials.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: cross-coupling; heterocycles; organic materials; oxidation; rhodium

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