4.7 Article

Copper-catalyzed tandem annulation of 2-alkynoyl-2′-iodo-1,1′-biphenyls with isocyanoacetates: a rapid access to pyrrole-fused tetracyclic skeletons

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 11, Pages 2456-2460

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0qo01657h

Keywords

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Funding

  1. National Natural Science Foundation of China [21772066, 22001093, 21971087]
  2. Key-Area Research and Development Program of Guangdong Province [2020B010188001]
  3. Guangdong Special Support Program [2017TX04R059]

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An efficient and convenient method for the synthesis of pyrrole-fused tetracyclic skeletons is described in this study, utilizing CuI as a catalyst. The reaction involves tandem [3 + 2] cycloaddition and C-C coupling processes to form 7-membered cyclic ketones fused with pyrrole and biphenyl rings.
An efficient and convenient synthesis of pyrrole-fused tetracyclic skeletons is presented. In this protocol using CuI as a catalyst, 1,1 '-biphenyl substrates with 2-alkynoyl and 2 '-iodo groups react with isocyanoacetates to provide 7-membered cyclic ketones fused with pyrrole and biphenyl rings through tandem [3 + 2] cycloaddition and C-C coupling processes.

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