5 years ago

Utilizing Glycerol as an Ex Situ CO-Source in Pd-Catalyzed Alkoxycarbonylation of Styrenes

Utilizing Glycerol as an Ex Situ CO-Source in Pd-Catalyzed Alkoxycarbonylation of Styrenes
Dennis U. Nielsen, Benjamin A. Wahlqvist, Dorrit B. Nielsen, Troels Skrydstrup, Kim Daasbjerg
We report on an efficient Ir-catalyzed decarbonylation of glycerol, which could be coupled to an ensuing Pd-catalyzed alkoxycarbonylation of styrenes. The formation of hydrogen could be avoided by employing 1,4-benzoquinone (BQ) as an external oxidant. A wide variety of styrenes underwent the esterification in good yields and high regioselectivity. Applying catalytic amounts of hexafluoroisopropanol provided access to alcohols other than methanol, which this transformation is often limited to. Finally, we demonstrate the suitability of this methodology for the preparation of three well-known nonsteroidal anti-inflammatory drugs (NSAIDs).

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b02179

DOI: 10.1021/acscatal.7b02179

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