Ligand Promoted meta-C–H Chlorination of Anilines and Phenols

Pd-catalyzed meta-C–H chlorination of anilines and phenols is developed using norbornene as the mediator. Heterocycles, including indole, thiophene, and indazole, are tolerated. The identification of a new pyridone-based ligand is crucial for the success of this meta-C–H chlorination reaction. Subse...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 138; no. 45; pp. 14876 - 14879
Main Authors Shi, Hang, Wang, Peng, Suzuki, Shin, Farmer, Marcus E, Yu, Jin-Quan
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.11.2016
Amer Chemical Soc
Subjects
Aniline Compounds - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Halogenation
Hydrocarbons, Chlorinated - chemical synthesis
Hydrocarbons, Chlorinated - chemistry
Ligands
Molecular Structure
Palladium - chemistry
Phenols - chemistry
Physical Sciences
Science & Technology
AROMATIC FUNCTIONALIZATION
CROSS-COUPLING REACTIONS
NORBORNENE
PALLADIUM-CATALYZED SYNTHESIS
ALKYLATION
ARYLATION
AMINO-ACID LIGANDS
BOND ACTIVATION
TEMPLATE
ARYL CHLORIDES
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Summary:Pd-catalyzed meta-C–H chlorination of anilines and phenols is developed using norbornene as the mediator. Heterocycles, including indole, thiophene, and indazole, are tolerated. The identification of a new pyridone-based ligand is crucial for the success of this meta-C–H chlorination reaction. Subsequent diverse transformations of the chlorinated products demonstrate the versatility of meta-C–H chlorination.
Bibliography:Medline
NIH RePORTER
ObjectType-Article-1
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content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b11055