Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 21, Pages 14177-14185Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01710
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Funding
- National Natural Science Foundation of China [22078299, 22108250]
- Zhejiang Provincial Natural Science Foundation of China [LY21B060005, LQ20B060007]
- Opening Project of Zhejiang Engineering Research Center of Fat-soluble Vitamin [202101]
- Zhejiang Provincial Department of Education [Y201840109]
- College of Pharmaceutical Sciences, Zhejiang University of Technology
- Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals
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In this study, a photoredox-catalyzed radical cascade reaction was developed for the efficient synthesis of 4-hydroxyalkyl-3,3-difluoro-gamma-lactams. The reaction demonstrated good tolerance towards various functional groups, required lower photocatalyst loading, and was easy to perform.
The photoredox-catalyzed radical difluoroalkylation/ cyclization/hydroxylation cascade reaction of various 2-bromo-2,2-difluoro-N-arylacetamides containing unactivated alkene moieties has been developed, providing green and efficient access to various 4-hydroxyalkyl-3,3-difluoro-gamma-lactams. Control experiments confirmed a radical process, and inexpensive air acted as the sole hydroxy resource. In addition, the highlights of this protocol include good tolerance for a variety functional groups, lower photocatalyst loading, and ease of operation.
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