期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 1, 页码 417-425出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b11097
关键词
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资金
- Scripps Research Institute
- NIH (NIGMS) [2R01 GM102265]
- Jiangxi Normal University
- Jiangxi Provincial Association of Science and Technology
A Pd-catalyzed, meta-selective C-H arylation of nosylprotected phenethylamines and benzylamines is disclosed using a combination of norbornene and pyridine-based ligands. Subjecting nosyl protected 2-aryl anilines to this protocol led to meta-C-H arylation at the remote aryl ring. A diverse range of aryl iodides are tolerated in this reaction, along with select heteroaryl iodides. Select aryl bromides bearing ortho-coordinating groups can also be utilized as effective coupling partners in this reaction. The use of pyridine ligands has allowed the palladium loading to be reduced to 2.5 mol %. Furthermore, a catalytic amount of 2-norbornene (20 mol %) to mediate this meta-C-H activation process is demonstrated for the first time. Utilization of a common protecting group as the directing group for meta-C-H activation of amines is an important feature of this reaction in terms of practical applications.
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