Enabling Reductive C-N Cross-Coupling of Nitroalkanes and Boronic Acids by Steric Design of P(III)/P(V)âO Catalysts.
J Am Chem Soc
; 144(18): 8242-8248, 2022 05 11.
Article
en En
| MEDLINE
| ID: mdl-35499970
ABSTRACT
An organophosphorus-catalyzed C-N bond-forming reductive coupling of nitroalkanes with arylboronic acids and esters is reported. The method shows excellent chemoselectivity for the nitro/boronic acid substrate pair, allowing the synthesis of N-(hetero)arylamines rich in functionalization. The identification of a sterically reduced phosphetane catalyst capable of productive coupling in the P(III)/P(V)âO redox manifold is the key enabling development. Combined experimental kinetics and computational mechanistic studies show that the sterically reduced catalyst affects post-rate-limiting steps to enable the C-N coupling event in preference to deleterious side-paths.
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Ácidos Borónicos
/
Nitrocompuestos
Idioma:
En
Año:
2022
Tipo del documento:
Article