Organic Letters
Letter
(10) Cu and Au catalyzed three-component reactions: (a) Yan, B.;
Liu, Y. Org. Lett. 2007, 9, 4323. (b) Albaladejo, M. J.; Alonso, F.; Yus,
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ASSOCIATED CONTENT
* Supporting Information
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S
(11) Palladium catalyzed cyclizations: (a) Chai, D. I.; Lautens, M. J.
Org. Chem. 2009, 74, 3054. (b) Ye, S.; Liu, J.; Wu, J. Chem. Commun.
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The Supporting Information is available free of charge on the
Experiment details and spectroscopic data (PDF)
(12) Barluenga, J.; Lonzi, G.; Riesgo, L.; Lop
́ ́
ez, L. A.; Tomas, M. J.
Am. Chem. Soc. 2010, 132, 13200.
(13) Yang, Y.-Z.; Xie, C.-S.; Xie, Y.-H.; Zhang, Y.-H. Org. Lett. 2012,
14, 957.
AUTHOR INFORMATION
Corresponding Authors
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(14) For selected reviews, see: (a) Biju, A. T.; Kuhl, N.; Glorius, F.
Acc. Chem. Res. 2011, 44, 1182. (b) Nair, V.; Menon, R. S.; Biju, A. T.;
Sinu, C. R.; Paul, R. R.; Jose, A.; Sreekumar, V. Chem. Soc. Rev. 2011,
40, 5336. (c) Grossmann, A.; Enders, D. Angew. Chem., Int. Ed. 2012,
51, 314. (d) Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511.
(e) Flanigan, D. M.; Romanov-Michailidis, F.; White, N. A.; Rovis, T.
Chem. Rev. 2015, 115, 9307.
ORCID
Author Contributions
(15) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719.
(16) For selected examples of NHC catalyzed direct functionaliza-
tions: (a) Chan, A.; Scheidt, K. A. J. Am. Chem. Soc. 2006, 128, 4558.
(b) Liu, Q.; Perreault, S.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 14066.
(c) Fang, X.; Chen, X.; Lv, H.; Chi, Y. R. Angew. Chem., Int. Ed. 2011,
50, 11782. (d) Biju, A. T.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49,
9761.
All authors have given approval to the final version of the
manuscript.
Notes
The authors declare no competing financial interest.
(17) For selected examples of NHC catalyzed β-functionalizations:
(a) Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126,
14370. (b) Nair, V.; Vellalath, S.; Poonoth, M.; Suresh, E. J. Am. Chem.
Soc. 2006, 128, 8736. (c) Lathrop, S. P.; Rovis, T. J. Am. Chem. Soc.
2009, 131, 13628. (d) Cardinal-David, B.; Raup, D. E. A.; Scheidt, K.
A. J. Am. Chem. Soc. 2010, 132, 5345.
(18) (a) Mohan, D. C.; Ravi, C.; Pappula, V.; Adimurthy, S. J. Org.
Chem. 2015, 80, 6846. (b) Liu, R.-R.; Hong, J.-J.; Lu, C.-J.; Xu, M.;
Gao, J.-R.; Jia, Y.-X. Org. Lett. 2015, 17, 3050.
(19) (a) Bailly, C. Curr. Med. Chem.: Anti-Cancer Agents 2004, 4, 363.
(b) Sharma, V.; Kumar, V. Med. Chem. Res. 2014, 23, 3593.
(20) (a) Wang, S.-N.; Li, X.-M.; Liu, H.-W.; Xu, L.; Zhuang, J.-C.; Li,
J.; Li, H.; Wang, W. J. Am. Chem. Soc. 2015, 137, 2303. (b) Chen, J.; Li,
J.-J.; Wang, J.-Z.; Li, H.; Wang, W.; Guo, Y.-W. Org. Lett. 2015, 17,
2214.
(21) 32% in CH3CN, 54% in THF, 47% in CHCl3, 35% in
ClCH2CH2Cl, 21% in DMF.
(22) (a) Okubo, T.; Yoshikawa, R.; Chaki, S.; Okuyama, S.;
Nakazato, A. Bioorg. Med. Chem. 2004, 12, 423. (b) Du, B.; Shan, A.;
Zhang, Y.; Zhong, X.; Chen, D.; Cai, K. Am. J. Med. Sci. 2014, 347,
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(23) Wang, H.-G.; Wang, Y.; Liang, D.-D.; Liu, L.-Y.; Zhang, J.-C.;
Zhu, Q. Angew. Chem., Int. Ed. 2011, 50, 5678.
(24) For the related studies, see: (a) Liang, D.-D.; He, Y.-M.; Liu, L.-
Y.; Zhu, Q. Org. Lett. 2013, 15, 3476. (b) Rao, D. N.; Rasheed, S.;
Vishwakarma, R. A.; Das, P. RSC Adv. 2014, 4, 25600.
ACKNOWLEDGMENTS
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Financial support of this research from the program for the
National Science Foundation of China (21372073, 21572054,
and 21572055), the Fundamental Research Funds for the
Central Universities, and the China 111 Project is gratefully
acknowledged.
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