Photodecarboxylative C-H Alkylation of Azauracils with N-(Acyloxy)phthalimides.
Org Lett
; 25(20): 3739-3744, 2023 May 26.
Article
de En
| MEDLINE
| ID: mdl-37184284
ABSTRACT
We disclose a transition-metal-free NaI/PPh3-mediated direct C-H alkylation of azauracils using N-(acyloxy)pthalimides (NHPIs) as readily available alkyl surrogates under visible light irradiation. Detailed mechanistic studies reveal formation of a photoactivated electron donor-acceptor (EDA) complex between NaI/PPh3, TMEDA, and alkyl NHPI ester and establish the crucial role of TMEDA in increasing the activity of the photoredox system. The reaction demonstrates a broad scope, scalability, and appreciable functional group tolerance. A variety of azauracils are shown to undergo alkylation by primary, secondary, and tertiary NHPI esters under mild conditions, furnishing the desired products in good to excellent yields.
Texte intégral:
1
Collection:
01-internacional
Base de données:
MEDLINE
Langue:
En
Journal:
Org Lett
Sujet du journal:
BIOQUIMICA
Année:
2023
Type de document:
Article
Pays d'affiliation:
Inde