Visible-Light-Promoted Decarboxylative Alkylation/Cyclization of Vinylcycloalkanes.
J Org Chem
; 88(13): 8563-8575, 2023 Jul 07.
Article
de En
| MEDLINE
| ID: mdl-37339016
ABSTRACT
An efficient strategy for visible-light-promoted decarboxylative alkylation of vinylcyclopropanes with alkyl N-(acyloxy)phthalimide esters through the dual C-C bond and single N-O bond cleavage, employing triphenylphosphine and lithium iodide as the photoredox system to synthesize 2-alkylated 3,4-dihydronaphthalenes, has been established. This alkylation/cyclization involves a radical process and undergoes a sequence of N-(acyloxy)phthalimide ester single-electron reduction, N-O bond cleavage, decarboxylative, alkyl radical addition, C-C bond cleavage, and intramolecular cyclization. Moreover, using the photocatalyst Na2-Eosin Y instead of triphenylphosphine and lithium iodide, the vinyl transfer products are acquired when vinylcyclobutanes or vinylcyclopentanes are utilized as alkyl radical receptors.
Texte intégral:
1
Collection:
01-internacional
Base de données:
MEDLINE
Sujet principal:
Iodures
/
Lithium
Langue:
En
Journal:
J Org Chem
Année:
2023
Type de document:
Article
Pays d'affiliation:
Chine