Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 8, Pages 1856-1864Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201900108
Keywords
Homogeneous catalysis; Heterocycles; Oxidation; Gold; Synthetic methods
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Funding
- Russian Science Foundation [18-73-00026]
- Russian Science Foundation [18-73-00026] Funding Source: Russian Science Foundation
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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.
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