Palladium-Catalyzed Synthesis of β,β-Diaryl α,β-Unsaturated Ketones

Yi-lin Zheng; Li Xiao; Qiong Xie; Li-ming Shao

doi:10.1055/s-0037-1611354

Synthesis, Table of Contents

Synthesis 2019; 51(06): 1455-1465
DOI: 10.1055/s-0037-1611354

paper

Palladium-Catalyzed Synthesis of β,β-Diaryl α,β-Unsaturated Ketones

Yi-lin Zheng

^aDepartment of Medicinal Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Pudong New District, Shanghai 201203, P. R. of China

,

Li Xiao

^aDepartment of Medicinal Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Pudong New District, Shanghai 201203, P. R. of China

,

Qiong Xie

^aDepartment of Medicinal Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Pudong New District, Shanghai 201203, P. R. of China

,

Li-ming Shao*

^aDepartment of Medicinal Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Pudong New District, Shanghai 201203, P. R. of China

^bState Key Laboratory of Medical Neurobiology, Fudan University, 138 Yixueyuan Road, Shanghai 200032, P. R. of China Email: limingshao@fudan.edu.cn

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Abstract

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Abstract

We herein describe a versatile palladium-catalyzed synthesis of β,β-diaryl α,β-unsaturated ketones. A broad range of aryl halides react with β-arylbutanones to afford biologically useful, symmetrical and unsymmetrical ketones. The use of 4,5-diazafluoren-9-one and oxygen makes this one-pot reaction more applicable. A plausible mechanism involving palladium-catalyzed oxidative Heck-type cross-coupling is also proposed.

Key words

ketones - palladium - 4,5-diazafluoren-9-one - oxidation - cross-coupling

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References

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