Palladium-catalyzed denitrogenation/vinylation of benzotriazinones with vinylene carbonate

Jiang Nan; Qiong Huang; Xinran Men; Shuai Yang; Jing Wang; Yangmin Ma

doi:10.1039/D4CC00059E

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Palladium-catalyzed denitrogenation/vinylation of benzotriazinones with vinylene carbonate†

Jiang Nan,

*^ab Qiong Huang,^a Xinran Men,^a Shuai Yang,^a Jing Wang^a and Yangmin Ma^a

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* Corresponding authors

^a Key Laboratory of Chemical Additives for China National Light Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi’an 710021, China
E-mail: nanjiang@sust.edu.cn

^b Xi’an Key Laboratory of Antiviral and Antimicrobial-Resistant Bacteria Therapeutics Research, Xi’an, China

Abstract

Herein, a novel Pd-catalyzed denitrogenation/vinylation of benzotriazinones using vinylene carbonate as the vinylation reagent is reported. This transformation demonstrates an unprecedented skeletal editing approach, effectively converting N [double bond, length as m-dash] N to CC fragments in situ and synthesizing a collection of isoquinolinones with broad-spectrum functional group tolerance. Moreover, the quite concise reaction system and late-stage modification of bioactive molecules comprehensively underscore the practical potential of this protocol.

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Article information

DOI: https://doi.org/10.1039/D4CC00059E
Article type: Communication
Submitted: 05 Jan 2024
Accepted: 27 Feb 2024
First published: 28 Feb 2024

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Chem. Commun., 2024,60, 3571-3574

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Palladium-catalyzed denitrogenation/vinylation of benzotriazinones with vinylene carbonate

J. Nan, Q. Huang, X. Men, S. Yang, J. Wang and Y. Ma, Chem. Commun., 2024, 60, 3571 DOI: 10.1039/D4CC00059E

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Chemical Communications

Palladium-catalyzed denitrogenation/vinylation of benzotriazinones with vinylene carbonate†

Abstract

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Palladium-catalyzed denitrogenation/vinylation of benzotriazinones with vinylene carbonate

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