Synthesis of Redox-Active Phenanthrene-Fused Heteroarenes by Palladium-Catalyzed C-H Annulation

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Pd-catalyzed C-H annulation reactions of halo- and aryl-heteroarenes were developed using readily available o-bromobiaryls and o-dibromoaryls, respectively. A variety of five-membered heteroarenes rapidly provided the corresponding phenanthrene-fused heteroarenes, which led to the identification of phenanthro-pyrazole and thiazole as new, stable -2 V redox couples. The flexible syntheses and tunability of the redox potentials of these azole-fused phenanthrenes over a wide range are expected to facilitate their application as redox-active organic functional materials.
Publisher
AMER CHEMICAL SOC
Issue Date
2020-02
Language
English
Article Type
Article
Citation

ORGANIC LETTERS, v.22, no.4, pp.1280 - 1285

ISSN
1523-7060
DOI
10.1021/acs.orglett.9b04545
URI
http://hdl.handle.net/10203/276772
Appears in Collection
CH-Journal Papers(저널논문)
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