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Rh-Catalyzed Coupling of Acrylic/Benzoic Acids with α-Diazocarbonyl Compounds: An Alternative Route for α-Pyrones and Isocoumarins.

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A coupling of acrylic acids/benzoic acids with α-diazocarbonyl compounds has been realized by a combined catalytic system of rhodium catalyst and Zn(OAc)2 additive. The presence of Zn(OAc)2 obviously accelerates the… Click to show full abstract

A coupling of acrylic acids/benzoic acids with α-diazocarbonyl compounds has been realized by a combined catalytic system of rhodium catalyst and Zn(OAc)2 additive. The presence of Zn(OAc)2 obviously accelerates the C(sp2)-H activation and destructed the formation of carboxylic ester that is formed via a nucleophilic O-H insertion to metal carbenoid. The procedure featured mild reaction conditions and broad substrate scope, providing a straightforward approach to the synthesis of α-pyrones and isocoumarins without the transformation of carboxylic acids to the corresponding amides.

Keywords: benzoic acids; coupling acrylic; acids diazocarbonyl; catalyzed coupling; diazocarbonyl compounds; pyrones isocoumarins

Journal Title: Organic letters
Year Published: 2022

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