Synthesis 2015; 47(19): 2924-2930
DOI: 10.1055/s-0034-1378718
special topic
© Georg Thieme Verlag Stuttgart · New York

Hypervalent Iodine Mediated C–C Double Bond Activation: A Cascade Access to α-Keto Diacetates from Readily Available Cinnamic Acids

Le Liu
Tianjin Key Laboratory for Modern Drug Delivery and High Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China   Email: duyunfeier@tju.edu.cn   Email: kangzhao@tju.edu.cn
,
Daisy Zhang-Negrerie
Tianjin Key Laboratory for Modern Drug Delivery and High Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China   Email: duyunfeier@tju.edu.cn   Email: kangzhao@tju.edu.cn
,
Yunfei Du*
Tianjin Key Laboratory for Modern Drug Delivery and High Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China   Email: duyunfeier@tju.edu.cn   Email: kangzhao@tju.edu.cn
,
Kang Zhao*
Tianjin Key Laboratory for Modern Drug Delivery and High Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China   Email: duyunfeier@tju.edu.cn   Email: kangzhao@tju.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 01 April 2015

Accepted after revision: 03 May 2015

Publication Date:
24 June 2015 (eFirst)

Abstract

The reaction of cinnamic acids with (diacetoxyiodo)benzene in 1,2-dichloroethane in the presence of sulfuric acid provides an easy and direct access to the α-keto diacetate framework. This hypervalent iodine mediated oxidative reaction involves a tandem sequence of aryl migration, insertion of an oxygen atom, decarboxylation and diacetoxylation. A reaction mechanism is proposed and discussed in light of control experiments.

Supporting Information

 
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