Electrochemical Arylation of Aldehydes, Ketones, and Alcohols: from Cathodic Reduction to Convergent Paired Electrolysis

Sheng Zhang, Lijun Li, Jingjing Li, Jianxue Shi, Kun Xu, Wenchao Gao, Luyi Zong, Guigen Li, Michael Findlater

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Arylation of carbonyls, one of the most common approaches toward alcohols, has received tremendous attention, as alcohols are important feedstocks and building blocks in organic synthesis. Despite great progress, there is still a great gap to develop an ideal arylation method featuring mild conditions, good functional group tolerance, and readily available starting materials. We now show that electrochemical arylation can fill the gap. By taking advantage of synthetic electrochemistry, commercially available aldehydes (ketones) and benzylic alcohols can be readily arylated to provide a general and scalable access to structurally diverse alcohols (97 examples, >10 gram-scale). More importantly, convergent paired electrolysis, the ideal but challenging electrochemical technology, was employed to transform low-value alcohols into more useful alcohols. Detailed mechanism study suggests that two plausible pathways are involved in the redox neutral α-arylation of benzylic alcohols.

Original languageEnglish
Pages (from-to)7275-7282
Number of pages8
JournalAngewandte Chemie - International Edition
Volume60
Issue number13
DOIs
StatePublished - Mar 22 2021

Keywords

  • arylation of alcohols
  • cathodic reduction
  • convergent paired electrolysis
  • reductive arylation of carbonyls

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