Propargylic Dialkyl Effect for Cyclobutene Formation through Ir(III)-Catalyzed Cycloisomerization of 1,6-Enynes.
Org Lett
; 26(4): 966-970, 2024 Feb 02.
Article
em En
| MEDLINE
| ID: mdl-38270400
ABSTRACT
The propargylic dialkyl effect (PDAE) has a significant impact on the cyclization reaction of enynes, partly reflected in changing the types of products. Herein, we described the influence of the propargylic dialkyl effect on the Ir(III)-catalyzed cycloisomerization of 1,6-enynes to provide strained cyclobutenes. A series of substituted 1,6-enynes were proved to be excellent substrate candidates in the presence of [Cp*IrCl2]2 in toluene. Mechanistic investigation, based on deuterium labeling experiments and control experiments, indicated that the propargylic dialkyl effect might boost C(sp)-H activation by preventing the coordination of active iridium species to the C(sp)≡C(sp) bond of enynes. This finding contributes to the fundamental understanding of enyne cyclization reactions and offers valuable insight into the propargylic dialkyl effect.
Texto completo:
1
Bases de dados:
MEDLINE
Idioma:
En
Revista:
Org Lett
Assunto da revista:
BIOQUIMICA
Ano de publicação:
2024
Tipo de documento:
Article
País de afiliação:
China