Organic Letters
Letter
decarboxylation22 of V followed by spontaneous oxidative
aromatization23 affords the substituted benzonitrile 3 or 4.
In conclusion, an expedient formal [4 + 2]-NHC-catalyzed
benzannulation has been developed. This strategy delivers
products containing medicinally relevant, cyano-bearing benzene
cores. Studies directed toward the development of other cyano-
binding medicinally important scaffolds are currently underway
in our laboratory.
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(17) (a) Zhao, X.; Ruhl, K. E.; Rovis, T. Angew. Chem., Int. Ed. 2012, 51,
12330. (b) De Sarkar, S.; Biswas, A.; Samanta, R. C.; Studer, A. Chem. -
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ASSOCIATED CONTENT
* Supporting Information
■
S
The Supporting Information is available free of charge on the
Experimental procedures and spectral data for all new
(18) Mo, J.; Chen, X.; Chi, Y. R. J. Am. Chem. Soc. 2012, 134, 8810.
(19) (a) De Sarkar, S.; Studer, A. Angew. Chem., Int. Ed. 2010, 49, 9266.
(b) Sun, F.-G.; Sun, L.-H.; Ye, S. Adv. Synth. Catal. 2011, 353, 3134.
(c) Sun, F.-G.; Sun, L.-H.; Ye, S. Adv. Synth. Catal. 2011, 353, 3134.
(20) An alternative cycloaddition pathway cannot be fully ruled out.
AUTHOR INFORMATION
Corresponding Author
■
Notes
(21) Samanta, R. C.; Maji, B.; De Sarkar, S.; Bergander, K.; Frohlich, R.;
̈
Muck-Lichtenfeld, C.; Mayr, H.; Studer, A. Angew. Chem., Int. Ed. 2012,
51, 5234.
̈
The authors declare no competing financial interest.
(22) (a) Nair, V.; Vellalath, S.; Poonoth, M.; Suresh, E. J. Am. Chem.
Soc. 2006, 128, 8736. (b) Chiang, P.-C.; Rommel, M.; Bode, J. W. J. Am.
Chem. Soc. 2009, 131, 8714. (c) Cardinal-David, B.; Raup, D. E. A.;
Scheidt, K. A. J. Am. Chem. Soc. 2010, 132, 5345. (d) Ryan, S. J.; Candish,
L.; Lupton, D. W. J. Am. Chem. Soc. 2011, 133, 4694.
(23) Izawa, Y.; Pun, D.; Stahl, S. S. Science 2011, 333, 209.
ACKNOWLEDGMENTS
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We thank the “Thousand Plan” program, Bayer Investigator
Fellow, Tsinghua-Peking Centre for Life Sciences (CLS), and
Tsinghua University for generous financial support.
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