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Synlett 2023; 34(17): 2005-2010
DOI: 10.1055/a-2109-0183
letter

Ruthenium(II)-Catalyzed C–H Annulation of Mandelic Acids with Internal Alkynes to Construct Isocoumarins

Shen Min Li∗
a   College of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China
,
Wang Huai Wang 
a   College of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China
,
Hong Jiang Li
a   College of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China
,
Fang Du
a   College of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China
,
Ying Na Cui∗
a   College of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China
,
Shu Jia Zhang
b   Guangxi Key Lab of Agricultural Resources Chemistry and Biotechnology, School of Chemistry and Food Science, Yulin Normal University, Guangxi Yulin 537000, P. R. of China
› Author AffiliationsThis work was financially supported by the Natural Science Foundation of Guangxi (project no. 2020GXNSFAA159125) and by the Science Foundation of Yulin Normal University (project no. G2019ZK17).
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Abstract

A series of isocoumarins were synthesized by a one-pot cyclization reaction with mandelic acids and internal alkynes as raw materials, [RuCl2(p-cymene)]2 as a catalyst, and Cu(OAc)2·H2O as an oxidant under reflux conditions in air. By using the established efficient and reliable reaction conditions, a range of substrates were explored, and it was found that both aromatic aldehydes and aromatic acids also reacted smoothly in this system to give moderate yields of the target products. Furthermore, the mandelic acids were shown to be converted into the corresponding benzoic acids as intermediates in the reaction.

Key words

ruthenium catalysis - mandelic acids - alkynes - annulation - isocoumarins

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2109-0183.
  • Supporting Information


Publication History

Received: 04 May 2023

Accepted after revision: 12 June 2023

Accepted Manuscript online:
12 June 2023

Article published online:
21 August 2023

© 2023. Thieme. All rights reserved

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