Synthesis of oxindoles through trifluoromethylation of N -aryl acrylamides by photoredox catalysis

Mild and direct intramolecular oxidative aryltrifluoromethylations of activated alkenes have been established through visible light photocatalysis, affording a range of CF 3 -containing oxindoles or isoquinolinediones in the presence of an organic fluorophore-type photocatalyst 4CzIPN, oxygen and vi...

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Published inOrganic & biomolecular chemistry Vol. 16; no. 35; pp. 6564 - 6568
Main Authors Lu, Maojian, Liu, Zhiji, Zhang, Jinwang, Tian, Yu, Qin, Honggui, Huang, Mingqiang, Hu, Shirong, Cai, Shunyou
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2018
Royal Society of Chemistry
Subjects
Alkenes
Aromatic compounds
Catalysis
Chemical synthesis
Chemistry
Chemistry, Organic
Functional groups
Irradiation
Light irradiation
Organic chemistry
Oxidizing agents
Photocatalysis
Photoredox catalysis
Physical Sciences
Radiation
Science & Technology
METAL-FREE SYNTHESIS
3-COMPONENT OXYTRIFLUOROMETHYLATION
SODIUM TRIFLUOROMETHANESULFINATE
ACTIVATED ALKENES
EOSIN Y
OXIDATIVE TRIFLUOROMETHYLATION
RADICAL ADDITIONS
HIGHLY EFFICIENT
UNACTIVATED ALKENES
CARBOXYLIC-ACIDS
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Summary:Mild and direct intramolecular oxidative aryltrifluoromethylations of activated alkenes have been established through visible light photocatalysis, affording a range of CF 3 -containing oxindoles or isoquinolinediones in the presence of an organic fluorophore-type photocatalyst 4CzIPN, oxygen and visible light irradiation under strong oxidant and transition metal free conditions. A variety of frequently encountered functional groups are well tolerated in this transformation.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/C8OB01922C