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Gold(I)-Catalyzed Oxidation of Acyl Acetylenes to Vicinal Tricarbonyls

Alexey Yu. Dubovtsev*, Dmitry V. Dar’in, Vadim Yu. Kukushkin*

*Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russian Federation, Email: a.dubovtsevspbu.ru, v.kukushkinspbu.ru

A. Y. Dubovtsev, D. V. Dar'in, V. Y. Kukushkin, Org. Lett., 2019, 21, 4116-4119.

DOI: 10.1021/acs.orglett.9b01297 (free Supporting Information)


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Abstract

An efficient gold(I)-catalyzed oxidation of COR2-functionalized internal alkynes provides α,β-diketoesters, 1,2,3-triketones, and α,β-diketoamides in good yields under mild conditions in the presence of 2,6-dichloropyridine N-oxide. The utility of these compounds was demonstrated by facile one-pot syntheses of azaheterocycles.

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Nature of the Nucleophilic Oxygenation Reagent Is Key to Acid-Free Gold-Catalyzed Conversion of Terminal and Internal Alkynes to 1,2-Dicarbonyls

A. Yu. Dubovtsev, N. V. Shcherbakov, D. V. Dar'in, V. Yu. Kukushkin, J. Org. Chem., 2020, 85, 745-757.


Key Words

1,2-diketones, keto esters and amides, pyridine N-oxides


ID: J54-Y2019