Visible-Light-Induced Regioselective Radical-Polar Crossover 1,4-Hydrophosphinylation of 1,3-Enynes: Access to Trisubstituted Allenes Bearing a Phosphine Oxide Group.
Org Lett
; 26(22): 4678-4683, 2024 Jun 07.
Article
en En
| MEDLINE
| ID: mdl-38787784
ABSTRACT
The radical 1,4-functionalizations of 1,3-enynes have emerged as a powerful strategy for the synthesis of multisubstituted allenes. However, the phosphorus-centered radical-initiated transformations remain largely elusive. Herein, visible-light photoredox catalytic regioselective radical hydrophosphinylation of 1,3-enynes with diaryl phosphine oxides as phosphinoyl radical precursors has been realized. This protocol features mild conditions, a wide substrate scope, and good functional group tolerance, producing a diverse range of phosphinoyl-substituted allenes in moderate to good yields with high atom economy. Detailed mechanistic experiments revealed a radical-polar crossover process in the reaction.
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Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Org Lett
/
Org. lett
/
Organic letters
Asunto de la revista:
BIOQUIMICA
Año:
2024
Tipo del documento:
Article
Pais de publicación:
Estados Unidos