Photoredox-catalyzed procedure for carbamoyl radical generation: 3,4-dihydroquinolin-2-one and quinolin-2-one synthesis

Wade F Petersen; Richard J K Taylor; James R Donald

doi:10.1039/c7ob01274h

Photoredox-catalyzed procedure for carbamoyl radical generation: 3,4-dihydroquinolin-2-one and quinolin-2-one synthesis

Wade F Petersen, Richard J K Taylor, James R Donald

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A reductive approach for carbamoyl radical generation from N-hydroxyphthalimido oxamides under photoredox catalysis is outlined. This strategy was applied to the synthesis of 3,4-dihydroquinolin-2-ones via the intermolecular addition/cyclization of carbamoyl radicals with electron deficient olefins in a mild, redox-neutral manner. Under a general set of reaction conditions, diversely substituted 3,4-dihydroquinolin-2-ones, including spirocyclic systems can be prepared. By using chlorine-substituted olefins, aromatic quinolin-2-ones can also be accessed.

Original language	English
Pages (from-to)	5831–5845
Number of pages	15
Journal	Organic and Biomolecular Chemistry
Volume	15
Issue number	27
DOIs	https://doi.org/10.1039/c7ob01274h
Publication status	Published - 30 Jun 2017

Bibliographical note

© The Royal Society of Chemistry 2017. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

Keywords

Journal Article

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10.1039/c7ob01274h

OBC Corrected Manuscript 20th June 2017
© The Royal Society of Chemistry 2017. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.
Accepted author manuscript, 2.37 MBLicence: Unspecified

Cite this

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Photoredox-catalyzed procedure for carbamoyl radical generation: 3,4-dihydroquinolin-2-one and quinolin-2-one synthesis

Abstract

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