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

Shen Min Li; Wang Huai Wang; Hong Jiang Li; Fang Du; Ying Na Cui; Shu Jia Zhang

doi:10.1055/a-2109-0183

Synlett, Inhaltsverzeichnis

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∗

^aCollege of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China

,

Wang Huai Wang

^aCollege of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China

,

Hong Jiang Li

^aCollege of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China

,

Fang Du

^aCollege of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China

,

Ying Na Cui∗

^aCollege of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China

,

Shu Jia Zhang

^bGuangxi Key Lab of Agricultural Resources Chemistry and Biotechnology, School of Chemistry and Food Science, Yulin Normal University, Guangxi Yulin 537000, P. R. of China

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Abstract

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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

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Referenzen

References and Notes
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