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

Haijian Wu, Jing Gui, Manman Sun*, Yongmin Ma, Jianguo Yang and Zhiming Wang*

*Advanced Research Institute and School of Pharmaceutical Sciences, Taizhou University, Jiaojiang, Zhejiang 318000, P. R. China, Email: sunmmtzc.edu.cn, zhimingtzc.edu.cn

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

DOI: 10.1021/acs.joc.3c00124

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Abstract

A palladium-catalyzed highly regioselective C-H allylation/annulation reaction of N-sulfonyl amides with secondary or tertiary allylic alcohols provides 3,4-dihydroisoquinolones bearing a synthetically valuable vinyl substituent. Commercially available allylic alcohol substrates, water as only by-product, and O₂ as terminal oxidant make the use of this process advantageous.

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proposed mechanism

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

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

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Key Words

3,4-dihydroisoquinolones, oxygen

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ID: J42-Y2023