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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 11: 3816 - 3823

DOI: https://doi.org/10.6023/cjoc202205039

ARTICLES

Synthesis of Esterified/Fused Isocoumarins via Rh-Catalyzed C—H Activation/Transannulative Coupling/Annulation of Phthalic Anhydrides with Cyclic 2-Diazo-1,3-diketones and Methanol

  • Mingzhou Shang ,
  • Lanlan Zhang ,
  • Miaomiao Chen ,
  • Wangcheng Hu ,
  • Xinwei He ,
  • Hongjian Lu
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  • aSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093
    bCollege of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000
*E-mail:

Received date: 2022-05-22

  Revised date: 2022-07-03

  Online published: 2022-07-14

Supported by

National Natural Science Foundation of China(21772001); National Natural Science Foundation of China(22071100); National Undergraduate Training Program for Innovation and Entrepreneurship(202110370035)

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Abstract

A rhodium(III)-catalyzed cascade reaction of phthalic anhydrides with cyclic 2-diazo-1,3-diketones and methanol for modular access to esterified cyclohexenone-fused isocoumarins has been developed. This strategy involves the process of one C—C and two C—O bonds formation through C—H activation, transannulative coupling and subsequent annulation process. Furthermore, no additive and base are needed in this transformation, and interestingly, the reaction could proceed well under air atmosphere with broad substrate and good functional groups tolerance.

Key words： annulation; C—H activation; diazo compound; isocoumarin; phthalic anhydride

Cite this article

Mingzhou Shang , Lanlan Zhang , Miaomiao Chen , Wangcheng Hu , Xinwei He , Hongjian Lu . Synthesis of Esterified/Fused Isocoumarins via Rh-Catalyzed C—H Activation/Transannulative Coupling/Annulation of Phthalic Anhydrides with Cyclic 2-Diazo-1,3-diketones and Methanol[J]. Chinese Journal of Organic Chemistry, 2022 , 42(11) : 3816 -3823 . DOI: 10.6023/cjoc202205039

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