Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp2)-H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes.
J Am Chem Soc
; 143(37): 14998-15004, 2021 09 22.
Article
em En
| MEDLINE
| ID: mdl-34491051
ABSTRACT
An iron-catalyzed C-H functionalization of simple monosubstituted allenes is reported. An efficient protocol for this process was made possible by the use of a newly developed electron-rich and sterically hindered cationic cyclopentadienyliron dicarbonyl complex as the catalyst and N-sulfonyl hemiaminal ether reagents as precursors to iminium ion electrophiles. Under optimized conditions, the use of a mild, functional-group-tolerant base enabled the conversion of a range of monoalkyl allenes to their allenylic sulfonamido 1,1-disubstituted derivatives, a previously unreported and contrasteric regiochemical outcome for the C-H functionalization of electronically unbiased and directing-group-free allenes.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Alcadienos
/
Hidrocarbonetos
/
Ferro
Idioma:
En
Ano de publicação:
2021
Tipo de documento:
Article