Organic Letters
Letter
(12) For recent advances in the Cu-mediated nitrogen-directed C−H
functionalization by other groups, see: (a) Chen, X.; Hao, X.-S.;
Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790.
(b) Uemura, T.; Imoto, S.; Chatani, N. Chem. Lett. 2006, 35, 842.
(c) Tran, L. D.; Popov, I.; Daugulis, O. J. Am. Chem. Soc. 2012, 134,
ASSOCIATED CONTENT
* Supporting Information
Detailed experimental procedures and characterization data of
compounds. This material is available free of charge via the
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S
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18237. (d) Urones, B.; Martínez, A. M.; Rodríguez, N.; Arrayas, R. G.;
Carretero, J. C. Chem. Commun. 2013, 49, 11044. (e) Shang, M.; Sun, S.-
Z.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 3354. (f) Li, Q.;
Zhang, S.-Y.; He, G.; Ai, Z.; Nack, W. A.; Chen, G. Org. Lett. 2014, 16,
1764. See the SI for complete citations.
(13) For the selected picolinamide-directed C−H functionalization,
see: (a) Zaitsev, V. Z.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc.
2005, 127, 13154. (b) He, G.; Chen, G. Angew. Chem., Int. Ed. 2011, 50,
5192. (c) Zhang, L.-S.; Chen, G.; Wang, X.; Guo, Q.-Y.; Zhang, X.-S.;
Pan, F.; Chen, K.; Shi, Z.-J. Angew. Chem., Int. Ed. 2014, 53, 3899. See
the SI for complete citations.
AUTHOR INFORMATION
Corresponding Authors
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
This work was partly supported by Grants-in-Aid from the
MEXT and JSPS, Japan.
(14) See the SI for the dihedral angle between two phenyl rings in 1k,
which was calculated by DFT at the RB3LYP/6-31G(d) level of theory.
(15) Suess, A. M.; Ertem, M. Z.; Cramer, C. J.; Stahl, S. S. J. Am. Chem.
Soc. 2013, 135, 9797.
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(16) (a) Huffman, L. M.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 9196.
(b) King, A. E.; Brunold, T. C.; Stahl, S. S. J. Am. Chem. Soc. 2009, 131,
5044. (c) King, A. E.; Huffman, L. M.; Casitas, A.; Costas, M.; Ribas, X.;
Stahl, S. S. J. Am. Chem. Soc. 2010, 132, 12068. (d) Casitas, A.; Canta, M.;
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́
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(10) In the course of this study, Ess and Kurti reported an elegant
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̈
(24) Nakatsuka, M. Jpn. Kokai Tokkyo Koho 2010, JP 2010205982, A
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̈
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dx.doi.org/10.1021/ol501037j | Org. Lett. XXXX, XXX, XXX−XXX