Photocatalyzed cascade Meerwein addition/cyclization of N-benzylacrylamides toward azaspirocycles

A visible-light-induced cascade Meerwein addition/cyclization of alkenes involving C-F bond cleavage was developed. This method offers a rapid access to azaspirocyclic cyclohexadienones from N-benzylacrylamides via C-F bond cleavage applying H2O as an external oxygen source, allowing for the incorpo...

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Published inOrganic & biomolecular chemistry Vol. 16; no. 14; pp. 2406 - 2410
Main Authors Yuan, Li, Jiang, Sheng-Ming, Li, Zeng-Zeng, Zhu, Yong, Yu, Jian, Li, Lan, Li, Ming-Zhu, Tang, Shi, Sheng, Rui-Rong
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2018
Royal Society of Chemistry
Subjects
Alkenes
Chemistry
Chemistry, Organic
Cleavage
Light effects
Physical Sciences
Salts
Science & Technology
DIAZONIUM SALTS
PHOTOREDOX
DEAROMATIVE CYCLIZATION
RADICAL CYCLIZATION
ARYLATION
ARYLPROPIOLAMIDES
SPIROCYCLIZATION
METAL-FREE
ACCESS
TRIFLUOROMETHYLATION
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Summary:A visible-light-induced cascade Meerwein addition/cyclization of alkenes involving C-F bond cleavage was developed. This method offers a rapid access to azaspirocyclic cyclohexadienones from N-benzylacrylamides via C-F bond cleavage applying H2O as an external oxygen source, allowing for the incorporation of various aromatic moieties originating from aryldiazonium salts.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob00132d