Synlett 2019; 30(03): 329-332
DOI: 10.1055/s-0037-1611183
letter
© Georg Thieme Verlag Stuttgart · New York

Cyclopropenium-Activated DMSO for Swern-Type Oxidation

Tianfo Guo
,
Yu Gao
,
Zhenjiang Li*
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Road South, Nanjing 211816, P. R. of China   Email: guok@njtech.edu.cn   Email: zjli@njtech.edu.cn
,
Jingjing Liu
,
Kai Guo*
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Road South, Nanjing 211816, P. R. of China   Email: guok@njtech.edu.cn   Email: zjli@njtech.edu.cn
› Author Affiliations
This work was supported by the National Key Research and Development Program of China (2017YFC1104802), the National Natural Science Foundation of China (U1463201, 21522604), the Natural Science Foundation of Jiangsu Province, China (BK20150031), the Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), the project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), and the Top-Notch Academic Programs Project of Jiangsu Higher Education Institutions (TAPP), and the Postgraduate Research & Practice Innovation Program of Jiangsu Province.
Further Information

Publication History

Received: 12 November 2018

Accepted after revision: 07 January 2019

Publication Date:
18 January 2019 (online)


Abstract

Swern oxidation is widely used to convert alcohols into their corresponding carbonyl compounds. However, the conventional method with use of the volatile oxalyl chloride as an activator requires the reaction to be conducted below −60 °C. We discovered that 3,3-dichloro-1,2-diphenylcyclopropene (DDC) can be used as a new activator for Swern-type oxidations of alcohols, which can be conducted at −20 °C. This new protocol features mild and fast reactions with easy operation. Furthermore, the activator DDC is easy to handle, and diphenylcyclopropenone can be recovered quantitively. This new type of Swern oxidation shows a broad scope of substrates including benzylic, allylic, aliphatic, and biobased alcohols, and gives high yields of up to 93%.

Supporting Information