Skeletal Editing of Dibenzolactones to Fluorenes via Ni- or Pd-Catalyzed Decarboxylation.

J Org Chem

Department of Chemistry, Iowa State University, Ames, Iowa 50011, United States.

Published: July 2023

The skeletal editing of dibenzolactones to fluorenes by Ni- or Pd-catalyzed decarboxylation is reported. In contrast to previously reported intramolecular decarboxylative couplings, inductively electron-withdrawing substituents on the aryl carboxylate moiety and metal additives are not required. The decarboxylation reaction proceeds cleanly and can be applied to the skeletal editing of a natural product analogue. Mechanistic observations are consistent with stabilization of the carboxylate-ligated Ni complex over the Ni-carboxylate ion pair, which is the key factor in promoting the challenging decarboxylation step in the catalytic cycle.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10528846PMC
http://dx.doi.org/10.1021/acs.joc.3c00700DOI Listing

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