4
Tetrahedron Letters
2,2,6,6-tetramethylpiperidinyloxy (TEMPO), and only the
details of the X-ray analysis, characterization data of NMR and
HRMS for all compounds and copies of the 1H NMR, 13C NMR)
associated with this article can be found, in the online version, at
yield of 57% was afforded, which suggested that the reaction
preceeds a radical process. Based on these control reactions, a
plausible
reaction
mechanism for carbonylation of
diarylmethanes is proposed (Figure 1). The initial step of this
reaction involves the hemolytic cleavage of NBS by both
sunlight and reflux to generate free radical Br·. Then abstraction
of the benzylic hydrogen atom(s) of diarylmethanes A by radical
Br· in subsequent steps leads to the di/mono-brominated
References and notes
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In conclusion, a highly efficient and convenient method in
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Acknowledgments
We gratefully acknowledge funding from the National Natural
Science Foundation of China (Nos. 21372265 and 61271059), the
Scientific Research Foundation for the Returned Overseas
Chinese Scholars, State Education Ministry, the Natural Science
Foundation Project of CQ CSTC (No. cstc2013jcyjA0217), and
the Fundamental Research Funds for the Central Universities
(CQDXWL-2013-Z012).
Supplementary Material
CCDC 976668 (3h) and the data can be obtained free of
charge from The Cambridge Crystallographic Data Centre via
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Supplementary data (detailed experimental description,
optimization of reaction condition, mechanistic investigations
and the route for synthesis of 2-(3-benzoylphenoxy)propanamide,