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- Title
Organophotoredox‐Mediated Amide Synthesis by Coupling Alcohol and Amine through Aerobic Oxidation of Alcohol.
- Authors
Shah, Sk. Sheriff; Shee, Maniklal; Venkatesh, Yarra; Singh, Amit Kumar; Samanta, Samya; Singh, N. D. Pradeep
- Abstract
The combination of an organic photocatalyst [4CzIPN (1,2,3,5‐tetrakis(carbazol‐9‐yl)‐4,6 dicyanobenzene) or 5MeOCzBN (2,3,4,5,6‐pentakis(3,6‐dimethoxy‐9 H‐carbazol‐9‐yl)benzonitrile)], quinuclidine, and tetra‐n‐butylammonium phosphate (hydrogen‐bonding catalyst) was employed for amide bond formations. The hydrogen‐bonded OH group activated the adjacent C−H bond of alcohols towards hydrogen atom transfer (HAT) by a radical species. The quinuclidinium radical cation, generated through single‐electron oxidation of quinuclidine by the photocatalyst, employed to abstract a hydrogen atom from the α‐C−H bond of alcohols selectively due to a polarity effect‐produced α‐hydroxyalkyl radical, which subsequently converted to the corresponding aldehyde under aerobic conditions. Then the coupling of the aldehyde and an amine formed a hemiaminal intermediate that upon photocatalytic oxidation produced the amide.
- Subjects
ALCOHOL oxidation; AMIDE synthesis; ABSTRACTION reactions; PHOTOCATALYTIC oxidation; RADICAL cations
- Publication
Chemistry - A European Journal, 2020, Vol 26, Issue 17, p3703
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201904924