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Synlett 2021; 32(04): 387-390
DOI: 10.1055/s-0040-1707246
cluster
Radicals – by Young Chinese Organic Chemists
© Georg Thieme Verlag Stuttgart · New York

Direct Deoxygenative Intramolecular Acylation of Biarylcarboxylic Acids

Yantao Li
a   State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   Email: cjzhu@nju.edu.cn   Email: xie@nju.edu.cn
,
Wentao Xu
a   State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   Email: cjzhu@nju.edu.cn   Email: xie@nju.edu.cn
,
Chengjian Zhu∗
a   State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   Email: cjzhu@nju.edu.cn   Email: xie@nju.edu.cn
b   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, P. R. of China
,
Jin Xie∗
a   State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   Email: cjzhu@nju.edu.cn   Email: xie@nju.edu.cn
› Author AffiliationsWe thank the National Natural Science Foundation of China (Grant Nos. 21971108, 21971111, 21702098, 21732003 and 21672099), the Natural Science Foundation of Jiangsu Province (Grant No. BK20190006), the Fundamental Research Funds for the Central Universities (Grant No. 020514380176), Jiangsu Six Peak Talent Project, and start-up funds from Nanjing University for financial support.
Further Information

Publication History

Received: 23 June 2020

Accepted after revision: 19 July 2020

Publication Date:
21 August 2020 (online)

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Published as part of the Cluster Radicals – by Young Chinese Organic Chemists

Abstract

A photocatalyzed intramolecular cyclization is developed for the synthesis of fluorenones. In this photoredox reaction, triphenylphosphine is used as an inexpensive and effective deoxygenative reagent for biarylcarboxylic acids to give acyl radicals, which quickly undergo intramolecular radical cyclization. Reactions in the presence of air and continuous flow photoredox technology demonstrate the generality and practicality of this process.

Key words

photocatalytic - deoxygenation - triphenylphosphine - radical cyclization - flow chemistry

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707246.
  • Supporting Information
 

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