Fragment Couplings via CO2 Extrusion-Recombination: Expansion of a Classic Bond-Forming Strategy via Metallaphotoredox

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Abstract

In this study we demonstrate that molecular fragments, which can be readily coupled via a simple, in situ RO-C=OR bond-forming reaction, can subsequently undergo metal insertion-decarboxylation-recombination to generate Csp2-Csp3 bonds when subjected to metallaphotoredox catalysis. In this embodiment the conversion of a wide variety of mixed anhydrides (formed in situ from carboxylic acids and acyl chlorides) to fragment-coupled ketones is accomplished in good to high yield. A three-step synthesis of the medicinal agent edivoxetine is also described using this new decarboxylation-recombination protocol.

Original languageEnglish (US)
Pages (from-to)11938-11941
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number37
DOIs
StatePublished - Sep 23 2015

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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