Alkynes as synthetic equivalents of ketones and aldehydes: A hidden entry into carbonyl chemistry

Igor V. Alabugin, Edgar Gonzalez-Rodriguez, Rahul Kisan Kawade, Aleksandr A. Stepanov, Sergei F. Vasilevsky

Результат исследований: Материалы для журналаСтатья

3 Цитирования (Scopus)

Выдержка

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.

Язык оригиналаАнглийский
Номер статьи1036
ЖурналMolecules
Том24
Номер выпуска6
DOI
СостояниеОпубликовано - 1 янв 2019
Опубликовано для внешнего пользованияДа

Отпечаток

Alkynes
alkynes
Ketones
aldehydes
entry
Aldehydes
ketones
chemistry
Functional groups
Carbonyl compounds
carbonyl compounds
cascades
Oxidation
oxidation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Цитировать

Alkynes as synthetic equivalents of ketones and aldehydes : A hidden entry into carbonyl chemistry. / Alabugin, Igor V.; Gonzalez-Rodriguez, Edgar; Kawade, Rahul Kisan; Stepanov, Aleksandr A.; Vasilevsky, Sergei F.

В: Molecules, Том 24, № 6, 1036, 01.01.2019.

Результат исследований: Материалы для журналаСтатья

Alabugin, Igor V. ; Gonzalez-Rodriguez, Edgar ; Kawade, Rahul Kisan ; Stepanov, Aleksandr A. ; Vasilevsky, Sergei F. / Alkynes as synthetic equivalents of ketones and aldehydes : A hidden entry into carbonyl chemistry. В: Molecules. 2019 ; Том 24, № 6.
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