Synthesis 2023; 55(17): 2779-2785
DOI: 10.1055/a-2069-4269
paper
Special Issue Honoring Prof. Guoqiang Lin's Contributions to Organic Chemistry

Synthesis of Dibenzo[f,h]quinolines by Stepwise C–H Arylation of 2-Phenylpyridine and Reductive Cyclodehydrogenation

Authors

  • Yan-Qin He

    a   Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Photochemistry, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, 2 Bei Yi Jie, Zhong Guan Cun, Haidian District, Beijing 100190, P. R. of China
    b   Institute of BioPharmaceutical Research, Liaocheng University, Liaocheng, Shandong 252059, P. R. of China
  • Zhong-Qiu Li

    a   Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Photochemistry, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, 2 Bei Yi Jie, Zhong Guan Cun, Haidian District, Beijing 100190, P. R. of China
  • Yu-Wu Zhong

    a   Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Photochemistry, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, 2 Bei Yi Jie, Zhong Guan Cun, Haidian District, Beijing 100190, P. R. of China
    c   School of Chemical Sciences, University of Chinese Academy of Sciences, No.19(A) Yuquan Road, Shijingshan District, Beijing 100049, P. R. of China

This work was supported by the National Natural Science Foundation of China (22001106 and 21925112). Y.-Q.H. thanks the Youth Innovation Technology Project of Higher School in Shandong Province (No. 2021KJ099) for funding support. Z.-Q.L. acknowledges the support of a BMS Junior Fellowship from the Beijing National Laboratory for Molecular Sciences (BNLMS).


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Dedicated to Prof. Guo-Qiang Lin on the occasion of his 80th birthday.

Abstract

A synthetic approach to dibenzo[f,h]quinolines and their derivatives via stepwise ruthenium-catalyzed C–H arylation and potassium-mediated reductive cyclodehydrogenation from 2-phenylpyridine and aryl bromides, is presented. One dibenzo[f,h]quinoline derivative is used as a bidentate ligand to prepare a cyclometalated ruthenium complex. Two dibenzo[f,h]quinoline compounds and the ruthenium complex were characterized by single-crystal X-ray structural analysis.

Supporting Information



Publikationsverlauf

Eingereicht: 26. Februar 2023

Angenommen nach Revision: 05. April 2023

Accepted Manuscript online:
05. April 2023

Artikel online veröffentlicht:
08. Mai 2023

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