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Synthesis 2021; 53(09): 1619-1628
DOI: 10.1055/s-0040-1706000
paper

Regioselective Oxidative Cross-Coupling Reaction: Synthesis of Imidazo[1,2-a]pyridine Fluorophores

Xianglong Chu‡
a   School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China
,
Yadi Niu‡
a   School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China
,
Xiaodong Wang
b   Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, P. R. of China
,
Yunliang Lin
b   Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, P. R. of China
,
Fuwei Li
b   Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, P. R. of China
,
Chen Ma∗
a   School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China
› Author AffiliationsThe National Natural Science Foundation of China (No. 21572117) and the Key Technology Research and Development Program of Shandong­ (Nos. 2019JZZY021015 and 2019GHY112053) provided funding.
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Abstract

A rapid access to a series of N-heteroarene fluorophores has been developed on the basis of the palladium-catalyzed direct oxidative C–H/C–H coupling of imidazo[1,2-a]pyridines with thiophenes/furans. The photophysical properties–structure relationship was systematically investigated. The resulting N-heteroarene fluorophores present color-tunable emissions (λem: 431–507 nm in CH2Cl2) and high fluorescence quantum yields (up to 91% in CH2Cl2).

Key words

imidazo[1,2-a]pyridines - oxidative C–H/C–H coupling - fluorophores­ - regioselectivity - palladium

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706000.
  • Supporting Information


Publication History

Received: 14 October 2020

Accepted after revision: 21 November 2020

Article published online:
04 January 2021

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