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

doi:10.1055/s-0035-1561572

Synthesis, Table of Contents

Synthesis 2016; 48(09): 1359-1370
DOI: 10.1055/s-0035-1561572

paper

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

Authors

Siying Chong

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China Email: suyp51@nwnu.edu.cn Email: huyl@nwnu.edu.cn
Yingpeng Su*

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China Email: suyp51@nwnu.edu.cn Email: huyl@nwnu.edu.cn
Lili Wu

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China Email: suyp51@nwnu.edu.cn Email: huyl@nwnu.edu.cn
Weigang Zhang

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China Email: suyp51@nwnu.edu.cn Email: huyl@nwnu.edu.cn
Junyan Ma

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China Email: suyp51@nwnu.edu.cn Email: huyl@nwnu.edu.cn
Xiaowei Chen

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China Email: suyp51@nwnu.edu.cn Email: huyl@nwnu.edu.cn
Danfeng Huang

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China Email: suyp51@nwnu.edu.cn Email: huyl@nwnu.edu.cn
Ke-Hu Wang

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China Email: suyp51@nwnu.edu.cn Email: huyl@nwnu.edu.cn
Yulai Hu*

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China Email: suyp51@nwnu.edu.cn Email: huyl@nwnu.edu.cn

^bState Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China

Abstract

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Abstract

Trimethylchlorosilane was used as chlorine source for the α-chlorination of 1,3-dicarbonyl compounds with phenyliodonium diacetate as oxidant at room temperature. The reaction allows the selective synthesis of α-monochlorinated products from different kinds of 1,3-dicarbonyl compounds in good yield. The potential possibility of this conversion for bromination has also been investigated.

Key words

chlorination - 1,3-dicarbonyl compounds - phenyliodonium diacetate - trimethylchlorosilane - Umpolung strategy

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References

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Supplementary Material

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