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Beyond Benzoin Condensation: Trimerization of Aldehydes via Metal-Free Aerobic Oxidative Esterification of Aldehydes with Benzoin Products in the Presence of Cyanide

Authors
Kim, Yoo-JinKim, Na YeunCheon, Cheol-Hong
Issue Date
2-5월-2014
Publisher
AMER CHEMICAL SOC
Citation
ORGANIC LETTERS, v.16, no.9, pp.2514 - 2517
Indexed
SCIE
SCOPUS
Journal Title
ORGANIC LETTERS
Volume
16
Number
9
Start Page
2514
End Page
2517
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/98543
DOI
10.1021/ol5008845
ISSN
1523-7060
Abstract
An unusual trimerization of aldehydes in the presence of cyanide via metal-free aerobic oxidative esterification under ambient conditions is described. Various aromatic aldehydes provided the corresponding oxidative esterification products in good to excellent yields. Mechanistic studies suggested that this reaction would proceed via a two-step sequence: cyanide-catalyzed benzoin condensation of aldehydes and subsequent aerobic oxidative esterification of aldehydes with the resultant benzoin products. The usefulness of this protocol was further demonstrated by converting the resulting trimeric products into other biologically important compounds.
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