Mild Three-Step Consecutive C–H Activations

Herein, the Rh-catalyzed consecutive C–H bond olefination/annulation/olefination cascade, tandemly directed by sulfonamide and ester groups, has been developed under mild conditions with the assistance of 1-adamantane carboxylic acid. A seven-membered metallacycle including an ester group was prefer...

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Bibliographic Details
Published in:Organic letters 2022-05, Vol.24 (17), p.3118-3122
Main Authors: Liu, Yao-Yao, Qu, Yuan-Lu, Kang, Yan-Shang, Zhu, Yue-Lu, Sun, Wei-Yin, Lu, Yi
Format: Article
Language:English
Subjects:
Catalysis
Esters
Molecular Structure
Rhodium - chemistry
Sulfonamides
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Summary:Herein, the Rh-catalyzed consecutive C–H bond olefination/annulation/olefination cascade, tandemly directed by sulfonamide and ester groups, has been developed under mild conditions with the assistance of 1-adamantane carboxylic acid. A seven-membered metallacycle including an ester group was preferred to the five-membered one including a sulfonamide group for the third C–H activation. In this transformation, the Rh catalyst exhibits its high reactivity by catalyzing a triple C–H activation process with a low catalyst loading at 50 °C. This method can be applied in the construction of various pharmaceutical derivatives.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00620