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Trimethylchlorosilane-Mediated Mild α-Chlorination of 1,3-Dicarbonyl Compounds Promoted by Phenyliodonium Diacetate

Siying Chong, Yingpeng Su*, Lili Wu, Weigang Zhang, Junyan Ma, Xiaowei Chen, Danfeng Huang, Ke-Hu Wang, Yulai Hu*

*College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China, Email:,

S. Chong, Y. Su, L. Wu, W. Zhang, J. Ma, X. Chen, D. Huang, K.-H. Wang, Y. Hu, Synthesis, 2016, 48, 1359-1370.

DOI: 10.1055/s-0035-1561572

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Trimethylchlorosilane was used as chlorine source for the α-chlorination of 1,3-dicarbonyl compounds with phenyliodonium diacetate as oxidant at room temperature to provide α-monochlorinated products in good yield. TMSBr could be used to form monobromide products.

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Key Words

α-chlorination (ketones, esters), chlorination, 1,3-dicarbonyl compounds, phenyliodonium diacetate, trimethylchlorosilane, Umpolung strategy

ID: J66-Y2016