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Visible light promoted and chlorophyll catalyzed α-oxidation of amines to amides under aerobic conditions: Synthesis of 3,4-dihydroisoquinolin-1(2H)-ones and N-phenyl oxalamides.
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Jul2023, Vol. 124, pN.PAG-N.PAG. 1p. - Publication Year :
- 2023
-
Abstract
- A visible-light-promoted α-oxidation of amines to amides is reported. Natural pigment chlorophyll is used as photosensitizer to generate singlet molecular oxygen 1O 2 as oxidants. [Display omitted] A novel method for the metal-free synthesis of 3,4-dihydroisoquinolin-1(2H)-ones and N -phenyl oxalamides from 1,2,3,4-tetrahydronisoquinoline and N -phenyl glycine derivatives based on visible-light photoredox catalysis under aerobic conditions is reported. Natural pigment chlorophyll is used as photosensitizer to generate singlet molecular oxygen 1O 2 , which is involved in the aerobic α-oxidation of N -phenyl amines. The protocol provides amides in good yields at room temperature under mild conditions. Based on the experimental results, a plausible photoredox mechanism is proposed. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 124
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 164863548
- Full Text :
- https://doi.org/10.1016/j.tetlet.2023.154579