Umpolung Synthesis of Diarylmethylamines via Palladium- Catalyzed Arylation of N-Benzyl Aldimines

Li M., Yucel B., Jimenez J., Rotella M., Fu Y., Walsh P. J.

ADVANCED SYNTHESIS & CATALYSIS, cilt.358, sa.12, ss.1910-1915, 2016 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 358 Sayı: 12
  • Basım Tarihi: 2016
  • Doi Numarası: 10.1002/adsc.201600075
  • Dergi Adı: ADVANCED SYNTHESIS & CATALYSIS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1910-1915
  • İstanbul Teknik Üniversitesi Adresli: Evet

Özet

An umpolung synthesis of diarylmethylamine derivatives is presented. This reaction entails a palladium-catalyzed arylation of 1,3-diaryl-2-azaallyl anions, in situ generated from N-benzyl aldimines. A Pd(NIXANTPHOS)-based catalyst together with hindered silylamide bases enabled the coupling of aldimines with aryl bromides in good to excellent yields without product isomerization. Moreover, regioselectivity in the arylation of unsymmetrical 1,3-diaryl-2-azaallyl anions was studied. This method is suitable for a gram scale synthesis of diarylmethylamine derivatives at room temperature without use of a glove box.