Organic Letters
Letter
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6) (a) Zhang, D.; Cui, X.; Zhang, Q.; Wu, Y. J. Org. Chem. 2015, 80,
517. (b) Xu, Y.; Liu, P.; Li, S.-L.; Sun, P. J. Org. Chem. 2015, 80, 1269.
c) Li, X.; Xu, Y.; Wu, W.; Jiang, C.; Qi, C.; Jiang, H. Chem.Eur. J.
014, 20, 7911. (d) Saidi, O.; Marafie, J.; Ledger, A. E. W.; Liu, P. M.;
Mahon, M. F.; Kociok-Kohn, G.; Whittlesey, M. K.; Frost, C. G. J. Am.
Chem. Soc. 2011, 133, 19298.
7) For selected reviews on copper-catalyzed/-mediated C(sp )−H
1
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2
̈
2
(
functionalization, see: (a) Allen, S. E.; Walvoord, R. R.; Padilla-Salinas,
R.; Kozlowski, M. C. Chem. Rev. 2013, 113, 6234. (b) Campbell, A. N.;
Stahl, S. S. Acc. Chem. Res. 2012, 45, 851. (c) Zhang, C.; Tang, C.; Jiao,
N. Chem. Soc. Rev. 2012, 41, 3464. (d) Wendlandt, A. E.; Suess, A. M.;
Stahl, S. S. Angew. Chem., Int. Ed. 2011, 50, 11062. (e) Daugulis, O.;
Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074.
2
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8) For examples on copper-catalyzed/mediated C(sp )−H
functionalization reactions, 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) Peng, J.; Chen,
M.; Xie, Z.; Luo, S.; Zhu, Q. Org. Chem. Front. 2014, 1, 777. (d) Peng,
J.; Xie, Z.; Chen, M.; Wang, J.; Zhu, Q. Org. Lett. 2014, 16, 4702.
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e) Hao, X.-Q.; Chen, L.-J.; Ren, B.; Li, L.-Y.; Yang, X.-Y.; Gong, J.-F.;
Niu, J.-L.; Song, M.-P. Org. Lett. 2014, 16, 1104.
9) For pioneering work on the use of the 8-aminoquinoline auxiliary,
see: (a) Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc.
(
2
005, 127, 13154. (b) Shabashov, D.; Daugulis, O. J. Am. Chem. Soc.
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010, 132, 3965. (c) For a recent review, see: Rouquet, G.; Chatani,
N. Angew. Chem., Int. Ed. 2013, 52, 11726.
10) For selected examples of Cu-mediated C−H functionalization
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directed by AQ, see: (a) Tran, L. D.; Popov, I.; Daugulis, O. J. Am.
Chem. Soc. 2012, 134, 18237. (b) Truong, T.; Klimovica, K.; Daugulis,
O. J. Am. Chem. Soc. 2013, 135, 9342. (c) Nishino, M.; Hirano, K.;
Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2013, 52, 4457. (d) Suess,
A. M.; Ertem, M. Z.; Cramer, C. J.; Stahl, S. S. J. Am. Chem. Soc. 2013,
1
35, 9797. (e) Wang, Z.; Ni, J.-Z.; Kuninobu, Y.; Kanai, M. Angew.
Chem., Int. Ed. 2014, 53, 3496. (f) Wu, X.; Zhao, Y.; Zhang, G.; Ge, H.
Angew. Chem., Int. Ed. 2014, 53, 3706. (g) Katayev, D.; Pfister, K. F.;
Wendling, T.; Gooβen, L. J. Chem.Eur. J. 2014, 20, 9902. (h) Dong,
J.; Wang, F.; You, J. Org. Lett. 2014, 16, 2884 and references cited
therein.
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11) For examples of Cu-mediated C−H functionalization directed
by PIP, see: (a) Li, B.; Liu, B.; Shi, B.-F. Chem. Commun. 2015, 51,
093. (b) Yin, X.-S.; Li, Y.-C.; Yuan, J.; Gu, W.-J.; Shi, B.-F. Org. Chem.
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Front. 2015, 2, 119. (c) Liu, Y.-J.; Liu, Y.-H.; Yin, X.-S.; Gu, W.-J.; Shi,
B.-F. Chem.Eur. J. 2015, 21, 205. (d) Chen, F.-J.; Liao, G.; Li, X.;
Wu, J.; Shi, B.-F. Org. Lett. 2014, 16, 5644. (e) Li, X.; Liu, Y.-H.; Gu,
W.-J.; Li, B.; Chen, F.-J.; Shi, B.-F. Org. Lett. 2014, 16, 3904.
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12) For examples of Cu-mediated C−H functionalization directed
by an amide-tethered oxazoline, see: (a) Wang, H.-L.; Shang, M.; Sun,
S.-Z.; Zhou, Z.-L.; Laforteza, B. N.; Dai, H.-X.; Yu, J.-Q. Org. Lett.
2
015, 17, 1228. (b) Shang, M.; Wang, H.-L; Sun, S.-Z.; Dai, H.-X.; Yu,
J.-Q. J. Am. Chem. Soc. 2014, 136, 11590. (c) Shang, M.; Sun, S.-Z.;
Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 3354.
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13) (a) Liu, Y.-J.; Zhang, Z.-Z.; Yan, S.-Y.; Liu, Y.-H.; Shi, B.-F.
Chem. Commun. 2015, 51, 7899. (b) Yan, S.-Y.; Liu, Y.-J.; Liu, B.; Liu,
Y.-H.; Zhang, Z.-Z.; Shi, B.-F. Chem. Commun. 2015, 51, 7341. (c) Liu,
Y.-J.; Liu, Y.-H.; Yan, S.-Y.; Shi, B.-F. Chem. Commun. 2015, 51, 6388.
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2
d) Yan, S.-Y.; Liu, Y.-J.; Liu, B.; Liu, Y.-H.; Shi, B.-F. Chem. Commun.
015, 51, 4069.
14) During the preparation of this manuscript, a copper-mediated
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2
sulfonylation of C(sp )−H bonds was reported; see: Liu, J.; Yu, L.;
Zhuang, S.; Gui, Q.; Chen, X.; Wang, W.; Tan, Z. Chem. Commun.
2
(
015, 51, 6418.
15) Chen, F.-J.; Zhao, S.; Hu, F.; Chen, K.; Zhang, Q.; Zhang, S.-Q.;
Shi, B.-F. Chem. Sci. 2013, 4, 4187.
16) (a) Zhang, H.; Yao, B.; Zhao, L.; Wang, D.-X.; Xu, B.-Q.; Wang,
(
M.-X. J. Am. Chem. Soc. 2014, 136, 6326. (b) Wang, Z.-L.; Zhao, L.;
Wang, M.-X. Org. Lett. 2011, 13, 6560. (c) King, A. E.; Huffman, L.
M.; Casitas, A.; Costas, M.; Ribas, X.; Stahl, S. S. J. Am. Chem. Soc.
2
2
010, 132, 12068. (d) Huffman, L. M.; Stahl, S. S. J. Am. Chem. Soc.
008, 130, 9196.
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Org. Lett. XXXX, XXX, XXX−XXX