Organic Letters
Letter
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(cinnamoyloxy)copper A was formed in the presence of
DABCO and at the same time radical B would be generated
by heating AIBME. Addition of the radical B at the α-position
of the double bond in A would give the benzylic radical C,
which then proceeds via an elimination of carbon dioxide and
Cu(I) to generate the product. The Cu(I) was oxidized by
Ag3PO4 to regenerate Cu(II) species.
In summary, we have successfully developed an efficient
copper-catalyzed oxidative decarboxylation coupling with
cinnamic acids, unsaturated ketoacids, and dimethyl 2,2′-
azobis(2-methylpropionate) (AIBME) to give the correspond-
ing β,γ-unsaturated carboxylic esters with high selectivity, in
which AIBME has been identified as a useful alkylcarboxylic
source. The reaction proceeded well to give the desired
products in moderate to good yields with complete stereo-
selectivity, which provided an easy access to β,γ-unsaturated
esters. Further studies to apply this strategy are in progress in
our laboratory.
ASSOCIATED CONTENT
* Supporting Information
■
S
The Supporting Information is available free of charge on the
X-ray crystallographic data (CIF)
Experimental procedures, characterization data, and
copies of NMR spectra (PDF)
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This research was supported by the Chinese Academy of
Sciences, the National Natural Science Foundation of China
(21222203, 21372231, and 21133011).
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(11) CCDC 1419100 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge from
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