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Synthesis 2021; 53(09): 1636-1644
DOI: 10.1055/a-1343-5642
paper

C2-gem-Aryldifluoromethylation of Quinoline N-Oxides with Potassium 2,2-Difluoro-2-arylacetates under Transition-Metal-Free Conditions

Yanhui Gao
a   Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education, Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China
,
Laiqiang Li
a   Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education, Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China
,
Jie Liu∗
a   Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education, Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China
,
Lei Wang
a   Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education, Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China
b   Advanced Research Institute and Department of Chemistry, Taizhou University, Taizhou, Zhejiang, 318000, P. R. of China
,
Min Wang∗
a   Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education, Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China
› Author AffiliationsWe gratefully acknowledge the National Natural Science Foundation of China (21901081), the Natural Science Foundation of Anhui Province (2008085QB90), and the Excellent Young Talents Fund Program of Higher Education Institutions of Anhui Province, China (gxyq2019167) for financial support.
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Abstract

A simple protocol for C2-gem-aryldifluoromethylation of quinoline N-oxides with potassium 2,2-difluoro-2-arylacetates has been developed, affording C2-gem-aryldifluoromethylated quinoline N-oxides bearing different functional groups in moderate to good yields. Moreover, experimental studies reveal that this reaction is likely to proceed through a radical pathway.

Key words

quinolone N-oxides - potassium 2,2-difluoro-2-aryl­acetates - CF2 group

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1343-5642.
  • Supporting Information


Publication History

Received: 13 December 2020

Accepted after revision: 28 December 2020

Accepted Manuscript online:
28 December 2020

Article published online:
25 January 2021

© 2020. Thieme. All rights reserved

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