The Effect of Basic Ligands and Alkenes on the Regioselectivity of C-H Additions of Tertiary Amines to Alkenes.
Chemistry
; 30(32): e202401014, 2024 Jun 06.
Article
in En
| MEDLINE
| ID: mdl-38570881
ABSTRACT
Highly regioselective C-H alkylation reactions of tertiary anilines and tertiary alkyl amines with simple alkenes have been achieved by the use of imidazolin-2-iminato scandium alkyl complexes. This protocol provided an efficient and atom-economical route to structurally diverse tertiary amine derivatives. The basic ligand, a coordinating THF in the catalyst and the substitution of alkene substrates were found to switch the regioselectivity of the C-H alkylation reactions of tertiary anilines presumably due to the generation of different types of catalytically active species or the formation of relatively stable intermediates. On the basis of the deuterium labeling experiments and KIE experiments, possible catalytical cycles were provided to understand the reaction mechanism as well as the regioselectivity.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Chemistry
Journal subject:
QUIMICA
Year:
2024
Document type:
Article
Affiliation country:
China
Country of publication:
Germany