Organic Letters
Letter
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In conclusion, we have developed an efficient and novel
synthetic approach to N-acylamidine involving an N−O bond
cleavage triggered rearrangement. This method uses readily
available starting materials and proceeds under mild reaction
conditions. The C−C bond of α-imino carbene is cleaved for
the first time. Two new C−N bonds and a C−O bond are
formed in the transformation. Full elucidation of the
mechanism is currently underway in our laboratory.
ASSOCIATED CONTENT
* Supporting Information
■
S
Experimental procedures, characterization data, and NMR
spectra for new compounds. This material is available free of
(11) Parr, B. T.; Green, S. A.; Davies, H. M. J. Am. Chem. Soc. 2013,
135, 4716.
(12) Yang, J.-M.; Zhu, C.-Z.; Tang, X.-Y.; Shi, M. Angew. Chem., Int.
Ed. 2014, 53, 5142.
(13) Spangler, J. E.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135,
6802.
AUTHOR INFORMATION
Corresponding Author
■
(14) (a) Selander, N.; Worrell, B. T.; Chuprakov, S.; Velaparthi, S.;
Fokin, V. V. J. Am. Chem. Soc. 2012, 134, 14670. (b) Miura, T.;
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work was generously supported by the National Natural
Science Foundation of China (21002091, 21372204) and the
Program for Innovative Research Team of Zhejiang Sci-Tech
University (13060052-Y).
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