Palladium-Catalyzed Cycloaddition of Alkynylimines, Double Isocyanides, and H2O/KOAc.
J Org Chem
; 85(10): 6441-6449, 2020 05 15.
Article
in En
| MEDLINE
| ID: mdl-32321251
ABSTRACT
In this work, a palladium-catalyzed cyclization of alkynylimines and double isocyanides is described. This facile procedure is efficient for synthesizing various 4-amidyl-2-aminopyrroles. Mechanism investigation indicates that a four-membered ring-fused pyrrole species is a key intermediate and the reaction involves [4 + 1] cycloaddition, protonation, nucleophilic addition, 1,4-addition of isocyanide, and rearomatization. Interestingly, the linear dipyrrole derivative is found to be an appropriate fluoride ion probe with a remarkable emission change, which could serve as a potential candidate for optoelectronic conjugated materials.
Full text:
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Database:
MEDLINE
Language:
En
Journal:
J Org Chem
Year:
2020
Type:
Article
Affiliation country:
China