Ligand-Enabled Meta-C–H Alkylation and Arylation Using a Modified Norbornene

2-Carbomethoxynorbornene is identified as a more effective transient mediator to promote a Pd­(II)-catalyzed meta-C­(sp2)–H alkylation of amides with various alkyl iodides as well as arylation with previously incompatible aryl iodides. The use of a tailor-made quinoline ligand is also crucial for th...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 137; no. 36; pp. 11574 - 11577
Main Authors Shen, Peng-Xiang, Wang, Xiao-Chen, Wang, Peng, Zhu, Ru-Yi, Yu, Jin-Quan
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.09.2015
Amer Chemical Soc
Subjects
Alkylation
amides
Chemistry
Chemistry, Multidisciplinary
Hydrocarbons, Cyclic - chemistry
iodides
Ligands
Norbornanes - chemistry
Physical Sciences
quinoline
Science & Technology
FUNCTIONALIZATION
HALIDES
ACTIVATION
OLEFINATION
ACIDS
ARENES
BOND FORMATION
SP
INDOLES
PALLADIUM-CATALYZED ALKYLATION
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Summary:2-Carbomethoxynorbornene is identified as a more effective transient mediator to promote a Pd­(II)-catalyzed meta-C­(sp2)–H alkylation of amides with various alkyl iodides as well as arylation with previously incompatible aryl iodides. The use of a tailor-made quinoline ligand is also crucial for this reaction to proceed.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.5b08914