Publication Type Journal Article
Title Gold-Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-Pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles
Authors Alexey Yu. Dubovtsev Dmitry V. Dar in Mikhail Krasavin V. Yu. Kukushkin
Groups CCC
Journal EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Year 2019
Month February
Volume
Number 8
Pages 1856-1864
Abstract Internal alkynes have been shown to undergo oxidation to substituted benzils (1,2-diarylethane-1,2-diones) by alpha-picoline N-oxide in the presence of Ph3PAuNTf2 (5 mol-\%). In addition to the unsubstituted benzil, the method allows preparing, under markedly mild conditions (50 degrees C in chlorobenzene), various non-symmetrical products, including heteroaromatic versions thereof which are much more difficult to obtain otherwise. This gold(I)-catalyzed transformation was integrated into one-pot reaction sequence delivering a range of 5- to 7-membered ring systems (imidazoles, quinoxalines, 1,2,4-triazines, pyrazines, and 1,4-diazepines), thus linking these important heterocyclic motifs to the internal alkyne reagent space.
DOI http://dx.doi.org/10.1002/ejoc.201900108
ISBN
Publisher
Book Title
ISSN 1434-193X
EISSN 1099-0690
Conference Name
Bibtex ID ISI:000459932200023
Observations
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