Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 26, Pages 3830-3836Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201700648
Keywords
Synthetic methods; Heterocycles; alpha-Keto acids; Sulfur; Selenium
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Funding
- National Council for Scientific and Technological Development (CNPq)
- Foundation for Research of the State of Rio Grande do Sul (FAPERGS)
- Coordination of Training of Higher Education Graduate Foundation (CAPES)
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Herein, we report the first decarboxylative oxidation of a-keto acids that is promoted by sodium metabisulfite (Na2S2O5) to obtain 2-substituted benzothiazoles and benzoselenazoles. Diaryl disulfides and diselenides were used as chalcogen sources, and the desired products were obtained in moderate to excellent yields. This protocol does not require an inert gas, transition metals, or harsh reaction conditions, and CO2 is released as an environmentally benign coproduct. The presence of Na2S2O5 was essential to guarantee that the reaction reached completion and afforded maximum product yields.
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