Electrochemical synthesis of β-hydroxy-, β-alkoxy-, and β-carbonyloxy sulfones by vicinal difunctionalization of olefins

Publication date: Available online 13 April 2019Source: Chinese Chemical LettersAuthor(s): Zhefan Zhang, Jiyao Yan, Dengke Ma, Jianwei SunAbstractAn electrochemical vicinal heterodifunctionalization of olefins for the synthesis of β-oxysulfones is described. With suitable choice of the conditions, including current, electrodes, and electrolyte, this oxidation reaction proceeded efficiently in an undivided cell without the use of a stoichiometric chemical oxidant. In addition to the previously established synthesis of β-hydroxysulfones in the presence of water, minor modification of this protocol by using either external alcohol nucleophiles or internal carboxylic acid nucleophile also led to the synthesis of β-alkoxysulfones, and β-sulfonyl lactones.Graphical abstractDisclosed here is an oxidant-free vicinal oxysulfonylation of olefins using electrochemical conditions.
Source: Chinese Chemical Letters - Category: Chemistry Source Type: research