Iron-Catalyzed Synthesis of Indenones through Cyclization of Carboxamides with Alkynes


ILIES L., Arslanoglu Y., MATSUBARA T., NAKAMURA E.

ASIAN JOURNAL OF ORGANIC CHEMISTRY, vol.7, no.7, pp.1327-1329, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 7 Issue: 7
  • Publication Date: 2018
  • Doi Number: 10.1002/ajoc.201800200
  • Journal Name: ASIAN JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1327-1329
  • Keywords: alkynes, amides, C-H activation, indenones, iron, H BOND FUNCTIONALIZATION, C-H, INTERNAL ALKYNES, AROMATIC CARBOXAMIDES, GRIGNARD-REAGENTS, ORGANIC-SYNTHESIS, AROYL CHLORIDES, ANNULATION, ACTIVATION, DERIVATIVES
  • Istanbul Technical University Affiliated: Yes

Abstract

The iron/diphosphine-catalyzed annulation of a carboxamide possessing a bidentate directing group with an internal alkyne proceeds in the presence of phenylzinc halide as a base at 40 degrees C to produce a variety of indenone derivatives. The reaction proceeds through iron-catalyzed C-H bond activation of the carboxamide, followed by insertion of the alkyne into the resulting iron intermediate, and cyclization accelerated by the presence of Lewis acidic Zn-II. The reaction of naphthalene and anthraceneamide yields pi-conjugated indenone derivatives.