Organic Letters
Letter
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In summary, a catalytic, selective, and convenient approach
to azoxyarene by oxidative coupling of secondary N-alkylani-
line has been developed. The reaction features broad substrate
scope and good functional group tolerance. Mechanistic
studies suggested that the cleavage of (alkyl)C−(aryl)N
bond took place first to release both primary aniline (or N-
hydroxylaniline) and aldehyde/ketone, followed by (aryl)N−
(aryl)N bond formation. Additionally, the azoxy can be viewed
as the bioisostere of alkene and amide, and several azoxyarene
products were discovered with anticancer activities.
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ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
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Experimental procedures, characterization data, kinetic
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studies, and H, 13C NMR, IR, and LC−MS analysis
Accession Codes
CCDC 1893754 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
AUTHOR INFORMATION
Corresponding Authors
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ORCID
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We acknowledge financial support provided by the National
Natural Science Foundation of China (21602011, 81572695).
We also thank Prof. Guangming Yao, Prof. Chaomei Xiong,
and Prof. Lingkui Meng (Huazhong University of Science and
Technology (HUST)) as well as the Analytical and Testing
Centre of HUST for NMR spectra and HRMS data collection.
We thank Prof. Qihui Chen (Fujian institute of Research on
the Structure of Matter, Chinese Academy of Science) for his
help with X-ray analysis.
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dinitroamino-4,4-azoxyfurazan and its derivatives: an Assembly of
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