Anodically Triggered Aldehyde Cation Autocatalysis for Alkylation of Heteroarenes

Alkylation of heteroarenes by using aldehydes is a direct approach to increase molecular complexity, which however often involves the use of stochiometric oxidant, strong acid, and high temperature. This study concerns an energy‐efficient electrochemical alkylation of heteroarenes by using aldehydes...

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Bibliographic Details
Published in:ChemSusChem 2020-04, Vol.13 (8), p.1997-2001
Main Authors: Liu, Caiyan, Xiao, Zihui, Wu, Shuhua, Shen, Yongli, Yuan, Kedong, Ding, Yi
Format: Article
Language:English
Subjects:
Aldehydes
Alkylation
Anode effect
Autocatalysis
Cations
electrochemistry
electrosynthesis
Energy conservation
heteroarenes
High temperature
Oxidizing agents
Regioselectivity
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Summary:Alkylation of heteroarenes by using aldehydes is a direct approach to increase molecular complexity, which however often involves the use of stochiometric oxidant, strong acid, and high temperature. This study concerns an energy‐efficient electrochemical alkylation of heteroarenes by using aldehydes under mild conditions without mediators. Interestingly, the graphite anode can trigger aldehyde cationic species, which act as the effective autocatalysts to react with a range of heteroarenes to produce the corresponding products with excellent regioselectivity and in high yields. Compared to the traditional electro‐synthesis approaches, this electro‐triggered reaction provides an electricity‐saving and eco‐friendly route to high‐value chemicals. Current affairs: A pulse of electrical current on anode‐triggered aldehyde cation species can autocatalyze the alkylation of heteroarenes to produce bis/tris(heteroaryl) alkane derivatives. Aromatic and aliphatic aldehydes are well compatible and react with N‐, O‐, and S‐heteroarenes to form valuable products with excellent regioselectivity in high yields. The simple but efficient electrochemical reaction exhibits excellent functional‐group tolerance under neutral and mild reaction conditions.
ISSN:1864-5631
1864-564X
DOI:10.1002/cssc.201903397