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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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
Wiley Subscription Services, Inc
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
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Abstract 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.
AbstractList 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 photoinduced radical difluoromethylation approach for the convenient synthesis of difluoromethylated oxindoles from N ‐arylacrylamides with difluoromethyl phenoxathiinium salt (PT‐CF 2 H + BF 4 − ) 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 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.
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.
Author Liu, Guo‐Kai
Long, Hong‐Xin
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Issue 48
Keywords Cascade reaction
Oxindole
Radical difluoromethylation
DESIGN
PHARMACEUTICALS
N-ARYLACRYLAMIDES
BIOISOSTERES
FLUORINATED 3,3-DISUBSTITUTED 2-OXINDOLES
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CATALYST
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Snippet A photocatalyst‐free photoinduced radical difluoromethylation approach for the convenient synthesis of difluoromethylated oxindoles from N‐arylacrylamides with...
A photocatalyst‐free photoinduced radical difluoromethylation approach for the convenient synthesis of difluoromethylated oxindoles from N ‐arylacrylamides...
A photocatalyst-free photoinduced radical difluoromethylation approach for the convenient synthesis of difluoromethylated oxindoles from N-arylacrylamides with...
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SubjectTerms Cascade chemical reactions
Cascade reaction
Chemical synthesis
Chemistry
Chemistry, Organic
Functional groups
Oxindole
Photocatalyst-free
Photocatalysts
Physical Sciences
Radical difluoromethylation
Science & Technology
Title Photocatalyst‐Free Visible‐Light Induced Radical Difluoromethylation/Cyclization Cascade Reaction for the Synthesis of Difluoromethylated Oxindoles with Difluoromethyl Phenoxathiinium Salt
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fejoc.202400948
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Volume 27
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