Photocatalyst‐Free Visible‐Light Induced Radical Difluoromethylation/Cyclization Cascade Reaction for the Synthesis of Difluoromethylated Oxindoles with Difluoromethyl Phenoxathiinium Salt

A photocatalyst‐free photoinduced radical difluoromethylation approach for the convenient synthesis of difluoromethylated oxindoles from N‐arylacrylamides with difluoromethyl phenoxathiinium salt (PT‐CF2H+BF4−) was developed, this transformation involves radical difluoromethylation/cyclization casca...

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Bibliographic Details
Published in:European journal of organic chemistry Vol. 27; no. 48
Main Authors: Long, Hong‐Xin, Liu, Guo‐Kai
Format: Journal Article
Language:English
Published: WEINHEIM Wiley 23.12.2024
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Subjects:
Cascade chemical reactions
Cascade reaction
Chemical synthesis
Chemistry
Chemistry, Organic
Functional groups
Oxindole
Photocatalyst-free
Photocatalysts
Physical Sciences
Radical difluoromethylation
Science & Technology
Cascade reaction
Oxindole
Radical difluoromethylation
DESIGN
PHARMACEUTICALS
N-ARYLACRYLAMIDES
BIOISOSTERES
FLUORINATED 3,3-DISUBSTITUTED 2-OXINDOLES
Photocatalyst-free
CATALYST
CYCLIZATION
ISSN:1434-193X, 1099-0690
Online Access:Get full text
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Summary:A photocatalyst‐free photoinduced radical difluoromethylation approach for the convenient synthesis of difluoromethylated oxindoles from N‐arylacrylamides with difluoromethyl phenoxathiinium salt (PT‐CF2H+BF4−) was developed, this transformation involves radical difluoromethylation/cyclization cascade process and features photocatalyst‐free, mild reaction conditions, broad substrate scope and good functional groups tolerance. With this method, a wide variety of N‐arylacrylamides were successfully converted to desired difluoromethylated oxindoles in good to excellent yields. A photocatalyst‐free visible‐light induced radical difluoromethylation approach for the convenient synthesis of difluoromethylated oxindoles from N‐arylacrylamides with difluoromethyl phenoxathiinium salt (PT‐CF2H+BF4−) was achieved. This transformation involves radical difluoromethylation/cyclization cascade process and features mild reaction conditions, broad substrate scope and good functional groups tolerance. Using this method, a wide range of difluoromethyl‐modified oxindoles was successfully synthesized in moderate to good yields.
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ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400948