Palladium-Catalyzed Regioselective C-H Functionalization/Annulation Reaction of Amides and Allylbenzenes for the Synthesis of Isoquinolinones and Pyridinones

Rong Zhong, Yong Xu, Manman Sun* and Yurong Wang*

*Taizhou University, 1139 Shifu Avenue, Taizhou 318000; Zhejiang Chinese Medical University, Hangzhou 310053, P. R. China, Email: sunmmtzc.edu.cn, yrwang1024hotmail.com

R. Zhong, Y. Xu, M. Sun, Y. Wang, J. Org. Chem., 2021, 86, 5255-5264.

DOI: 10.1021/acs.joc.1c00150

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Abstract

A palladium-catalyzed C(sp²)-H allylation/aminopalladation/β-H elimination/isomerization sequence enables an annulation reaction of N-sulfonyl amides and allylbenzenes to construct isoquinolinones and pyridinones in good yield in the presence of air as the terminal oxidant.

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proposed mechanism

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Palladium-Catalyzed C-H Allylation/Annulation Reaction of Amides and Allylic Alcohols: Regioselective Construction of Vinyl-Substituted 3,4-Dihydroisoquinolones

H. Wu, J. Gui, M. Sun, Y. Ma, J. Yang, Z. Wang, J. Org. Chem., 2023, 88, 3871-3882.

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Key Words

isoquinolinones, air

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ID: J42-Y2021