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Synlett 2000; 2000(2): 245-247
DOI: 10.1055/s-2000-6486
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Electrosynthesis of Benzolactones by Nickel-Catalyzed Carboxylation of Epoxide-Functionalized Aromatic Halides

Patricia Tascedda* , Elisabet Duñach
  • *Laboratoire de Chimie Bioorganique, Associé au CNRS, Université de Nice-Sophia Antipolis, 06108 Nice Cedex 2, France; Fax +33-4 92 07 61 51; E-mail: dunach@unice.fr
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Publication Date:
31 December 2000 (online)

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The electrochemical, nickel-catalyzed carbon dioxide incorporation into 2-haloaryl epoxides led chemoselectively to different carboxylated products according to the nature of the substrate and to the catalytic system. Whereas terminal epoxide derivatives led to cyclic carbonates in good yields, disubstituted epoxides reacted through a first carbon-halogen bond carboxylation followed by epoxide ring opening. Five-membered ring benzolactones were selectively formed with cyclam as the ligand, whereas 6-membered ring isocoumarine derivatives were obtained using 2,2′-bipyridine.

electrochemical - benzolactone - nickel - carbon dioxide - epoxide