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Photoredox-Catalyzed Reductive Carbamoyl Radical Generation: A Redox-Neutral Intermolecular Addition-Cyclization Approach to Functionalized 3,4-Dihydroquinolin-2-ones.

Authors :
Petersen WF
Taylor RJ
Donald JR
Source :
Organic letters [Org Lett] 2017 Feb 17; Vol. 19 (4), pp. 874-877. Date of Electronic Publication: 2017 Jan 30.
Publication Year :
2017

Abstract

The first reductive generation of carbamoyl radicals using photoredox catalysis for their formation is reported. This approach facilitated the development of a redox-neutral synthesis of functionalized 3,4-dihydroquinolin-2-ones via the novel intermolecular addition-cyclization of carbamoyl radicals across electron-deficient alkenes. To illustrate the versatility of this reaction, a diverse collection of 3,4-dihydroquinolin-2-ones, including fused cyclic and spirocyclic systems inspired by natural products, has been prepared.

Details

Language :
English
ISSN :
1523-7052
Volume :
19
Issue :
4
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
28135099
Full Text :
https://doi.org/10.1021/acs.orglett.7b00022