Selective mono-alkylation of N-methoxybenzamides

We report our latest discovery of norbornene derivative modulated highly mono-selective ortho-C-H activation alkylation reactions on arenes bearing simple mono-dentate coordinating groups. The reaction features the use of readily available benzamides and alkyl halides. During the study, we prepared...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 53; no. 30; pp. 4258 - 4261
Main Authors Chen, Zenghua, Hu, Le'an, Zeng, Fanyun, Zhu, Ranran, Zheng, Shasha, Yu, Qingzhen, Huang, Jianhui
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Subjects
Activation
Amides
Aromatic compounds
Benzamide
Chemistry
Chemistry, Multidisciplinary
Derivatives
Ligands
Physical Sciences
Science & Technology
Strategy
Utilization
FUNCTIONALIZATION
UNACTIVATED C(SP)-H BONDS
ACTIVATION
ARENES
ARYLATION
C(SP)-H
PD/NORBORNENE
C-H BONDS
DIRECTED ALKYLATION
PALLADIUM-CATALYZED ALKYLATION
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Summary:We report our latest discovery of norbornene derivative modulated highly mono-selective ortho-C-H activation alkylation reactions on arenes bearing simple mono-dentate coordinating groups. The reaction features the use of readily available benzamides and alkyl halides. During the study, we prepared 30 mono-alkylated aryl amides in good yields with good mono-selectivity. We have also demonstrated that structurally rigid alkenes such as norbornene and its derivatives are a good class of ligand and could be used for future direct C-H functionalizations. The utilization of norbornene type ligands for assistance in C-H activation processes has opened a new window for future molecular design using direct C-H functionalization strategies.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc01201b