Polarity Umpolung Strategy for the Radical Alkylation of Alkenes.
Angew Chem Int Ed Engl
; 59(21): 8195-8202, 2020 05 18.
Article
in En
| MEDLINE
| ID: mdl-32048420
ABSTRACT
Free radical mediated alkylation of alkenes is a challenging and largely unmet goal. Disclosed here is a conceptually novel "polarity umpolung" strategy for radical alkylation of alkenes using a portfolio of easily accessed, difunctional alkylating reagents. This strategy is achieved by substituting inherently nucleophilic alkyl radicals with electrophilic sulfone-bearing surrogates, thus inverting the usual mode of reactivity. Along with alkylation, either an heteroaryl or oximino group is concurrently incorporated into the alkenes by a consecutive docking and migration process, leading to valuable products. The reaction displays a broad functional-group tolerance under mild reaction conditions. The protocol opens new vistas for the late-stage modification of complex natural products and drug molecules containing alkene moieties.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Angew Chem Int Ed Engl
Year:
2020
Document type:
Article
Affiliation country:
China