Construction of 1-Heteroaryl-3-azabicyclo[3.1.0]hexanes by sp3-sp2 Suzuki-Miyaura and Chan-Evans-Lam Coupling Reactions of Tertiary Trifluoroborates.
Org Lett
; 19(9): 2450-2453, 2017 05 05.
Article
em En
| MEDLINE
| ID: mdl-28436667
ABSTRACT
Compounds that contain the 1-heteroaryl-3-azabicyclo[3.1.0]hexane architecture are of particular interest to the pharmaceutical industry yet remain a challenge to synthesize. We report herein an expedient and modular approach to the synthesis of 1-heteroaryl-3-azabicyclo[3.1.0]hexanes by Suzuki-Miyaura and Chan-Evans-Lam coupling reactions of tertiary trifluoroborate salts. Our Suzuki-Miyaura cross-coupling protocol is compatible with a broad range of aryl and heteroaryl bromides and chlorides. The unprecedented Chan-Evans-Lam coupling of tertiary trifluoroborates allows the facile construction of 1-heteroaryl-3-azabicyclo[3.1.0]hexanes containing C-tertiary arylamines at the ring juncture.
Texto completo:
1
Base de dados:
MEDLINE
Idioma:
En
Revista:
Org Lett
Assunto da revista:
BIOQUIMICA
Ano de publicação:
2017
Tipo de documento:
Article
País de afiliação:
Estados Unidos