Palladium-Catalyzed Carbonylative Synthesis of Aryl Selenoesters Using Formic Acid as an Ex Situ CO Source

A new catalytic protocol for the synthesis of selenoesters from aryl iodides and diaryl diselenides has been developed, where formic acid was employed as an efficient, low-cost, and safe substitute for toxic and gaseous CO. This protocol presents a high functional group tolerance, providing access t...

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Veröffentlicht in:Journal of organic chemistry 2022-01, Vol.87 (1), p.595-605
Hauptverfasser: Yano de Albuquerque, Danilo, Teixeira, Wystan K. O, Sacramento, Manoela do, Alves, Diego, Santi, Claudio, Schwab, Ricardo S
Format: Artikel
Sprache:eng
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Zusammenfassung:A new catalytic protocol for the synthesis of selenoesters from aryl iodides and diaryl diselenides has been developed, where formic acid was employed as an efficient, low-cost, and safe substitute for toxic and gaseous CO. This protocol presents a high functional group tolerance, providing access to a large family of selenoesters in high yields (up to 97%) while operating under mild reaction conditions, and avoids the use of selenol which is difficult to manipulate, easily oxidizes, and has a bad odor. Additionally, this method can be efficiently extended to the synthesis of thioesters with moderate-to-excellent yields, by employing for the first time diorganyl disulfides as precursors.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02608