Photoinduced Remote C(sp3)-H Cyanation and Oxidation Enabled by a Vinyl Radical-Mediated 1,5-HAT Strategy.
Org Lett
; 24(36): 6560-6565, 2022 09 16.
Article
in En
| MEDLINE
| ID: mdl-36069753
ABSTRACT
We report a vinyl radical-mediated 1,5-hydrogen atom transfer (1,5-HAT) strategy for the remote C(sp3)-H functionalization reaction, which includes cyanation, oxidation, and etherification under visible-light-induced photochemical conditions. This reaction is achieved using readily available alkyl N-hydroxyphthalimide esters as radical precursors, which can efficiently react with diverse alkynes to form key vinyl radical intermediates followed by a 1,5-HAT process. A series of structurally diverse γ-cyano, γ-carbonyl, and γ-oxygenated alkenes with excellent stereoselectivity can be efficiently constructed by this synthetic protocol.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Alkenes
/
Hydrogen
Language:
En
Journal:
Org Lett
Year:
2022
Document type:
Article