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

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

ASIAN JOURNAL OF ORGANIC CHEMISTRY, cilt.7, sa.7, ss.1327-1329, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 7 Sayı: 7
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1002/ajoc.201800200
  • Dergi Adı: ASIAN JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1327-1329
  • Anahtar Kelimeler: 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
  • İstanbul Teknik Üniversitesi Adresli: Evet

Özet

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.