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Synthesis 2024; 56(01): 47-54
DOI: 10.1055/s-0042-1751522
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Rh(III)-Catalyzed Synthesis of Isocoumarins via C–H Activation of Phenacyl Phosphoniums with Iodonium Ylides

Lu Jiang
a   School of Chemistry and Chemical Engineering, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018, P. R. of China
b   College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001, P. R. of China
,
Lei Gao
a   School of Chemistry and Chemical Engineering, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018, P. R. of China
b   College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001, P. R. of China
,
Xiaofei Li
b   College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001, P. R. of China
,
Tingting Shao
b   College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001, P. R. of China
,
Jinzhong Yao  ∗
b   College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001, P. R. of China
,
Maozhong Miao∗
a   School of Chemistry and Chemical Engineering, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018, P. R. of China
,
Hongwei Zhou  ∗
b   College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001, P. R. of China
› InstitutsangabenWe gratefully acknowledge the National Natural Science Foundation of China (Project No. 21606080, 22071082), the Natural Science Foundation of Zhejiang Province (No. LY19B020004), the Jiaxing Key Laboratory for Creation of Animal Models and Synthesis of Lead Compounds of New Drug (No. JXSZ21002), and the Science and Technology Project of Jiaxing (No. 2022AY10018).
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Abstract

A phosphonium-assisted C–H cyclization with iodonium ylides has been developed under redox-neutral rhodium(III) catalysis, offering a wide variety of valuable isocoumarins in moderate to good yields. This transformation proceeds through C–H activation, carbene insertion, and nucleophilic addition processes. The reaction occurs under a low catalyst loading in a short reaction time and does not require an oxidant.

Key words

rhodium - isocoumarins - phenacyl phosphoniums - iodonium ylides - C–H activation

Supporting Information



Publikationsverlauf

Eingereicht: 23. September 2023

Angenommen nach Revision: 19. Oktober 2023

Artikel online veröffentlicht:
23. November 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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