Organic Letters
Letter
Encyclopedia of Chemical Technology; Wiley-VCH Verlag: Weinheim,
Scheme 3. Proposed Mechanism on NaNO2-Catalyzed
Aerobic Bromination of Alkane under Visible Light
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with Br2, and HBr is reoxidized by NO2 to Br2. In fact, the
bromination could end when all bromine is consumed. In
general, the alkyl sp3C−H bond is brominated with Br−/
0.5O2/H+ to generate an alkyl sp3C−Br bond and H2O under
visible light.
In summary, we have established an aerobic bromination of
alkyl sp3C−H bonds of simple cycloalkanes and branch/linear
functional alkanes with KBr/air (O2) in the presence of
catalytic NaNO2 in 37% HCl (aq)/solvent under visible light
at room temperature to 40 °C. Alkyl bromides are usually
obtained in moderate to excellent yields based on KBr in these
catalytic reactions. Although an acidic solution is necessary in
the oxidative process, the use of air or O2 at normal pressure as
the terminal oxidant is always convenient and economic.
Further studies on the reaction mechanism, scope, and
application are underway.
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ASSOCIATED CONTENT
* Supporting Information
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S
The Supporting Information is available free of charge on the
Typical experimental procedures, detailed screening the
reaction conditions, preparations and characterization of
compounds and spectroscopic data (PDF)
AUTHOR INFORMATION
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Corresponding Author
ORCID
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
We thank the National Natural Science Foundation of China
(Grant No. 21372153) for financial support.
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REFERENCES
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1964, 56 (7), 44−65. (b) Mills, J. F. Bromine: in Ullmann’s
D
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