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DOI: 10.1055/s-0037-1611183
Cyclopropenium-Activated DMSO for Swern-Type Oxidation
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.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%.
Key words
alcohols - carbonyl compounds - cyclopropenium ion - geminal dichloro compounds - Swern oxidationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611183.
- Supporting Information
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References and Notes
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