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Electrochemical Formation of Cinnamaldehyde by the Electrolyte System N,N ‐Diisopropylethylamine and 1,1,1,3,3,3‐Hexafluoropropan‐2‐ol
Author(s) -
Imada Yasushi,
Okada Yohei,
Chiba Kazuhiro
Publication year - 2020
Publication title -
chemelectrochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.182
H-Index - 59
ISSN - 2196-0216
DOI - 10.1002/celc.202000275
Subject(s) - cinnamaldehyde , electrolyte , synthon , chemistry , electrochemistry , catalysis , organic chemistry , thio , combinatorial chemistry , electrode
The use of a supporting electrolyte has been a significant issue in electro‐organic chemistry because it can be wasteful and increase steps in terms of separation from target products. However, it is ideal for an electrolyte to play multiple roles in reactions, for example, as a feedstock or catalyst. We have discovered that the combination of N,N ‐diisopropylethylamine (DIPEA) and 1,1,1,3,3‐hexafluoropropan‐2‐ol (HFIP) not only works as an electrolyte but also facilitates the electrochemical formation of cinnamaldehyde from benzaldehydes. We demonstrate that the synthesis of 20 cinnamaldehyde derivatives can be achieved by using this reaction. Isotope‐labeling experiments and 13 C NMR investigations revealed the mechanistic aspects of this process, and confirmed that DIPEA is the C2 synthon of acetaldehyde and HFIP could also function as a Brønsted acid.