Burgess Reagent Facilitated Alcohol Oxidations in DMSO

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• 作者：Prakash R. Sultane ; Christopher W. Bielawski
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 20, 2017
• 年：2017
• 卷：82
• 期：2
• 页码：1046-1052
• 全文大小：439K
• ISSN：1520-6904

文摘

The Burgess reagent ([methoxycarbonylsulfamoyl]triethylammonium hydroxide) has historically found utility as a dehydrating agent. Herein we show that, in the presence of dimethyl sulfoxide, the Burgess reagent efficiently and rapidly facilitates the oxidation of a broad range of primary and secondary alcohols to their corresponding aldehydes and ketones in excellent yields and under mild conditions, and can be combined with other transformations (e.g., Wittig olefinations). A mechanism similar to those described for the Pfitzner–Moffatt and Swern oxidations is proposed.