Synthesis 2016; 48(09): 1359-1370
DOI: 10.1055/s-0035-1561572
paper
© Georg Thieme Verlag Stuttgart · New York

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

Siying Chong
a  College 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*
a  College 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
a  College 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
a  College 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
a  College 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
a  College 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
a  College 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
a  College 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*
a  College 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
b  State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 18 November 2015

Accepted after revision: 01 February 2016

Publication Date:
02 March 2016 (online)


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.

Supporting Information

 
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