Photoinduced synthesis of fluorinated dibenz[ b , e ]azepines via radical triggered cyclization

A simple, mild and efficient approach to access fluorinated dibenz[ b , e ]azepines via visible-light photoredox catalysis is presented. Inexpensive and commercially available fluoroalkyl anhydrides in concert with pyridine N -oxide are employed as the source of the fluoroalkyl radicals. A one-pot p...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 55; no. 73; pp. 10848 - 10851
Main Authors Qi, Xu-Kuan, Zhang, Hong, Pan, Zi-Tong, Liang, Rong-Bin, Zhu, Can-Ming, Li, Jing-Hong, Tong, Qing-Xiao, Gao, Xue-Wang, Wu, Li-Zhu, Zhong, Jian-Ji
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 10.09.2019
Royal Society of Chemistry
Subjects
Amines
anhydrides
azepines
catalytic activity
Chemistry
Chemistry, Multidisciplinary
Crystallography
cyclization reactions
Fluorination
free radicals
light
nitrogen oxides
Photoredox catalysis
Physical Sciences
pyridines
redox reactions
Science & Technology
FUNCTIONALIZATION
MIANSERIN
VISIBLE-LIGHT PHOTOCATALYSIS
EFFICIENT
PHOTOREDOX CATALYSIS
TRIFLUOROMETHYLATION
INSIGHTS
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Summary:A simple, mild and efficient approach to access fluorinated dibenz[ b , e ]azepines via visible-light photoredox catalysis is presented. Inexpensive and commercially available fluoroalkyl anhydrides in concert with pyridine N -oxide are employed as the source of the fluoroalkyl radicals. A one-pot process involving the trifluoroacetylation of unprotected secondary benzyl amines followed by radical cyclization could also afford the desired fluorinated dibenz[ b , e ]azepines.
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/C9CC04977K