Alkyl Carbazates for Electrochemical Deoxygenative Functionalization of Heteroarenes. (30th April 2020)

• Record Type: Journal Article
• Authors: Gao, Yongyuan; Wu, Zhengguang; Yu, Lei; Wang, Yi; Pan, Yi
• Is Part Of: Angewandte Chemie. Volume 132:Number 27(2020)
• Page Start: 10951
• Page End: 10955
• Publication Date: 2020-04-30
• Subjects: carbazate -- deoxgenative alkylation -- electrochemistry -- radical fragmentation; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202001571
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The C−O bond cleavage for activation of alcohols is synthetically useful and practically challenging. This work describes carbazate as a new type of electrochemically activated alkylating agent derived from ubiquitous alcohols for direct functionalization of heteroarenes under mild electrolytic conditions. The simple undivided cell at low oxidative potentials with carbon/platinum electrode set‐ups offers excellent substrate tolerance, affording a variety of primary, secondary and tertiary alkyl‐decorated heterocycles in good chemical yields. Furthermore, the mechanism for this electrochemical deoxyalkylation reaction has been investigated. Abstract : Carbazates are introduced as a new type of electrochemically activated alkylating agent for direct functionalization of heteroarenes under mild cell conditions.