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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 1: 242 - 248

DOI: https://doi.org/10.6023/cjoc202106023

ARTICLES

Rhodium-Catalyzed Directing Group-Assisted Annulation of Arene C—H Bond with Vinylene Carbonate toward Isocoumarins

  • Lu Wang ,
  • Ying Shao ,
  • Fan Chen ,
  • Pengcheng Qian ,
  • Jiang Cheng
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  • a School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164
    b College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035
* Corresponding authors. E-mail: ,

Received date: 2021-06-10

  Revised date: 2021-07-14

  Online published: 2021-09-03

Supported by

National Natural Science Foundation of China(21971025); Advanced Catalysis and Green Manufacturing Collaborative Innovation Center; “Innovation & Entrepreneurship Talents” Introduction Plan of Jiangsu Province, the Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology(BM2012110); Foundation of Wenzhou Science & Technology Bureau(W20170003)

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Abstract

Isocoumarins are an important pharmaceutical compounds. Many synthetic pathways have been developed, mainly focusing on the cyclization of benzoic acid or other with alkynes. Sulfinylidene benzamides were facilely prepared and developed in the chelation-assisted arene ortho-C—H functionalization, and vinylene carbonate can establish an oxidant-free catalytic system, giving carbonic acid as a sole side product. In the presence of rhodium catalyst, an annulation between sulfinylidene benzamides and vinylene carbonate was developed, proceeding with directing group-assisted ortho-C—H coupling and intramolecular alcoholysis toward nonsubstituted isocoumarins in moderate to good yields.

Key words： rhodium; sulfinylidene benzamides; vinylene carbonate

Cite this article

Lu Wang , Ying Shao , Fan Chen , Pengcheng Qian , Jiang Cheng . Rhodium-Catalyzed Directing Group-Assisted Annulation of Arene C—H Bond with Vinylene Carbonate toward Isocoumarins[J]. Chinese Journal of Organic Chemistry, 2022 , 42(1) : 242 -248 . DOI: 10.6023/cjoc202106023

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