BULLETIN OF THE
Article
Metal-Free Aerobic Oxidative Esterification of Aldehydes
KOREAN CHEMICAL SOCIETY
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6. For excellent examples of metal/additive-free aerobic oxidative
In addition, several different types of alcohols were utilized in
this oxidative esterification to afford the corresponding esters
in good to excellent yields. Moreover, this protocol could be
extended to the synthesis of thioesters using a thiol as an acyl
transfer nucleophile. Furthermore, the synthesis of lactones
via intramolecular metal-free aerobic oxidative esterification
was achieved based on this protocol in the absence of an
alcohol.
Although the similarity in reactivity between NHCs and
cyanide has been well-appreciated in carbon–carbon bond for-
mation reactions, there have not been as many examples of the
oxidative esterification of aldehydes with cyanide as those
with NHCs, which suggested that oxidative esterification of
aldehydes with cyanide might be relatively unexplored so
far. This study demonstrated that the cyanide-mediated
metal-free aerobic oxidative esterification of aldehydes was
not an unusual and isolated example, but a general and predict-
able protocol.
esterification of aldehydes with
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Acknowledgment.
We acknowledge the National
Research Foundation of Korea (NRF) grants (NRF-
2014M2A8A4021398 and NRF-20100020209).
SupportingInformation. Additionalsupportinginformation
is available in the online version of this article.
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Bull. Korean Chem. Soc. 2015, Vol. 36, 2055–2061
© 2015 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim