Intermolecular 1,2-Aminoboration of Alkynes and the Critical Role of Electron-Rich Alkynes.
Angew Chem Int Ed Engl
; : e202413370, 2024 Sep 23.
Article
em En
| MEDLINE
| ID: mdl-39312442
ABSTRACT
The intramolecular 1,2-aminoboration of alkynes by aminoboranes is rare and invariably requires a catalyst to proceed, while the intermolecular aminoboration of alkynes is yet entirely unknown. Through an exploration of the significance of electronics in alkynes for activating the B-N σ-bond of aminoboranes, we demonstrate in this work the first intermolecular 1,2-aminoboration of alkynes. These reactions employ a series of (amino)dihaloboranes and aminoboronic esters, mild reaction conditions, and no catalysts, yielding syn-addition alkene products with incorporation of two crucial functionalities amino and boryl. While highly electron-rich examples can afford the aminoborated products (Z)-2-borylethenamines, other alkynes, including unactivated and less electron-rich examples, do not lead to the corresponding aminoborated products due to the fundamental impediment that the reactions are significantly endergonic.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Ano de publicação:
2024
Tipo de documento:
Article
País de afiliação:
Alemanha
País de publicação:
Alemanha