Oxidative C–H/C–H Cross-Coupling of [1,2,4]Triazolo­[1,5‑a]­pyrimidines with Indoles and Pyrroles: Discovering Excited-State Intramolecular Proton Transfer (ESIPT) Fluorophores

A highly efficient Rh­(III)-catalyzed oxidative C–H/C–H cross-coupling of [1,2,4]­triazolo­[1,5-a]­pyrimidines (TAP) with indoles and pyrroles has been developed, which provides an opportunity to rapidly assemble a large library of novel excited-state intramolecular proton transfer (ESIPT) fluoropho...

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Bibliographic Details
Published in:Organic letters 2019-06, Vol.21 (11), p.4058-4062
Main Authors: Zhang, Mangang, Cheng, Rui, Lan, Jingbo, Zhang, Huaxing, Yan, Lipeng, Pu, Xingwen, Huang, Zhenmei, Wu, Di, You, Jingsong
Format: Article
Language:English
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Summary:A highly efficient Rh­(III)-catalyzed oxidative C–H/C–H cross-coupling of [1,2,4]­triazolo­[1,5-a]­pyrimidines (TAP) with indoles and pyrroles has been developed, which provides an opportunity to rapidly assemble a large library of novel excited-state intramolecular proton transfer (ESIPT) fluorophores. The resulting 7-(pyrrol-2-yl)­TAPs only show the enol-form emission, while 7-(indol-2-yl)­TAPs would undergo an ESIPT process and mainly exhibit the keto-form emission. In highly polar solvents, the enol-form emission of 7-(indol-2-yl)­TAPs is enhanced significantly, thus showing the dual emission of enol and keto forms.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01238