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Molecules 2019, 24(6), 1036; https://doi.org/10.3390/molecules24061036

Alkynes as Synthetic Equivalents of Ketones and Aldehydes: A Hidden Entry into Carbonyl Chemistry

1
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306, USA
2
Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Science, 630090 Novosibirsk, Russia
3
Novosibirsk State University, 2, Pirogova Str., 630090 Novosibirsk, Russia
*
Author to whom correspondence should be addressed.
Received: 18 February 2019 / Revised: 8 March 2019 / Accepted: 11 March 2019 / Published: 15 March 2019
(This article belongs to the Special Issue Alkynes: From Reaction Design to Applications in Organic Synthesis)

Abstract

The high energy packed in alkyne functional group makes alkyne reactions highly thermodynamically favorable and generally irreversible. Furthermore, the presence of two orthogonal π-bonds that can be manipulated separately enables flexible synthetic cascades stemming from alkynes. Behind these “obvious” traits, there are other more subtle, often concealed aspects of this functional group’s appeal. This review is focused on yet another interesting but underappreciated alkyne feature: the fact that the CC alkyne unit has the same oxidation state as the -CH2C(O)- unit of a typical carbonyl compound. Thus, “classic carbonyl chemistry” can be accessed through alkynes, and new transformations can be engineered by unmasking the hidden carbonyl nature of alkynes. The goal of this review is to illustrate the advantages of using alkynes as an entry point to carbonyl reactions while highlighting reports from the literature where, sometimes without full appreciation, the concept of using alkynes as a hidden entry into carbonyl chemistry has been applied. View Full-Text
Keywords: alkynes; carbonyl compounds; ketones; aldehydes; condensations; cyclizations; catalysis; nucleophilic addition; acetals; rearrangements; electronic structure alkynes; carbonyl compounds; ketones; aldehydes; condensations; cyclizations; catalysis; nucleophilic addition; acetals; rearrangements; electronic structure
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Alabugin, I.V.; Gonzalez-Rodriguez, E.; Kawade, R.K.; Stepanov, A.A.; Vasilevsky, S.F. Alkynes as Synthetic Equivalents of Ketones and Aldehydes: A Hidden Entry into Carbonyl Chemistry. Molecules 2019, 24, 1036.

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