Naphthylpyridyl-Cu(II)-Catalyzed Oxidative Coupling of 2-Naphthylamines to Access BINAM Derivatives

Naphthylpyridyl–Cu(II)-Catalyzed Oxidative Coupling of 2-Naphthylamines to Access BINAM Derivatives
  • Lee, Jonghyeon
  • Lee, Jooyeon
  • Kong, Minwoo
  • Kang, Jiwon
  • Lee, Daeyeon
  • ... Lee, Jeonghyo
  • 외 2명
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초록

In this study, we report the efficient synthesis of 1,1 '-binaphthyl-2,2 '-diamine (BINAM) derivatives via copper-catalyzed oxidative coupling of 2-aminonaphthalenes. The use of a ligand featuring an extended pi system in combination with Cu(II) and molecular oxygen as the terminal oxidant enabled the formation of various BINAM derivatives in yields of up to 84%. Mechanistic investigations suggest a redox pathway involving Cu(II)/Cu(I) cycling, and pi-pi interactions between the ligand and substrate are proposed to stabilize reactive intermediates, thereby contributing to the observed efficiency.

키워드

2 NaphthylamineCopperOxygen2 NaphthylamineCopperCupric IonDiamineOxygenArticleCatalysisControlled StudyDrug DevelopmentNonhumanOxidative CouplingSynthesisFACILE SYNTHESISCOMPLEXESLIGANDSACIDHYDROGENATIONACTIVATION
제목
Naphthylpyridyl-Cu(II)-Catalyzed Oxidative Coupling of 2-Naphthylamines to Access BINAM Derivatives
제목 (타언어)
Naphthylpyridyl–Cu(II)-Catalyzed Oxidative Coupling of 2-Naphthylamines to Access BINAM Derivatives
저자
Lee, JonghyeonLee, JooyeonKong, MinwooKang, JiwonLee, DaeyeonLee, JeonghyoKim, MinKang, Houng
DOI
10.1021/acs.orglett.5c02740
발행일
2025-08
유형
Article; Early Access
저널명
Organic Letters
27
33
페이지
9195 ~ 9200