Organic Letters
Letter
(7) Selected recent reviews on C−H activation: (a) Engle, K. M.; Mei,
T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788. (b) Hashiguchi,
B. G.; Bischof, S. M.; Konnick, M. M.; Periana, R. A. Acc. Chem. Res.
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(j) Ye, B.; Cramer, N. Acc. Chem. Res. 2015, 48, 1308.
and heretoaromatic-fused pyridine N-oxide derivatives. In
addition, the present protocol provides a straightforward
approach for the synthesis of phosphorylated heterocycles, an
important structural feature in organic synthesis and material
chemistry. During the course of the mechanistic investigations,
we isolated a rare dimer of bimetallic species containing two
iridacyclic units, which catalyzes the reaction without any
additives. Further studies on the dimeric Ir complex and studies
to expand this methodology for the synthesis of pyridine N-oxide
derivatives are currently underway in our laboratory.
(8) Li, B.; Jiao, P.; Zhong, H.; Huang, J. Synlett 2013, 24, 2431.
(9) (a) Shi, Z.; Koester, D. C.; Boultadakis-Arapinis, M.; Glorius, F. J.
Am. Chem. Soc. 2013, 135, 12204. (b) Sun, P.; Wu, Y.; Yang, T.; Wu, X.;
Xu, J.; Lin, A.; Yao, H. Adv. Synth. Catal. 2015, 357, 2469.
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
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(10) (a) Hu, F.; Xia, Y.; Ma, C.; Zhang, Y.; Wang, J. Chem. Commun.
2015, 51, 7986. (b) Cheng, Y.; Bolm, C. Angew. Chem., Int. Ed. 2015, 54,
12349. (c) Shi, L.; Yu, K.; Wang, B. Chem. Commun. 2015, 51, 17277.
(11) For selected examples of [Cp*IrCl2]2-catalyzed C−H activation,
see: (a) Ryu, J.; Kwak, J.; Shin, K.; Lee, D.; Chang, S. J. Am. Chem. Soc.
2013, 135, 12861. (b) Itoh, M.; Hirano, K.; Satoh, T.; Shibata, Y.;
Tanaka, K.; Miura, M. J. Org. Chem. 2013, 78, 1365. (c) Pan, S.; Wakaki,
T.; Ryu, N.; Shibata, T. Chem. - Asian J. 2014, 9, 1257. (d) Ai, W.; Yang,
X.; Wu, Y.; Wang, X.; Li, Y.; Yang, Y.; Zhou, B. Chem. - Eur. J. 2014, 20,
17653. (f) Kang, T.; Kim, Y.; Lee, D.; Wang, Z.; Chang, S. J. Am. Chem.
Soc. 2014, 136, 4141. (g) Xie, F.; Qi, Z.; Yu, S.; Li, X. J. Am. Chem. Soc.
2014, 136, 4780. (h) Kim, H.; Shin, K.; Chang, S. J. Am. Chem. Soc. 2014,
136, 5904. (i) Pan, C.; Jin, N.; Zhang, H.; Han, J.; Zhu, C. J. Org. Chem.
2014, 79, 9427. (j) Shin, K.; Chang, S. J. Org. Chem. 2014, 79, 12197.
(12) Selected recent examples of [Cp*IrCl2]2-catalyzed C−H
activation: (a) Ai, W.; Wu, Y.; Tang, H.; Yang, X.; Yang, Y.; Li, Y.;
Zhou, B. Chem. Commun. 2015, 51, 7871. (b) Chen, H.; Huestis, M. P.
ChemCatChem 2015, 7, 743. (c) Lee, D.; Chang, S. Chem. - Eur. J. 2015,
21, 5364. (d) Hou, W.; Yang, Y.; Ai, W.; Wu, Y.; Wang, X.; Zhou, B.; Li,
Y. Eur. J. Org. Chem. 2015, 2015, 395. (e) Wu, Y.; Yang, Y.; Zhou, B.; Li,
Y. J. Org. Chem. 2015, 80, 1946. (f) Wang, H.; Xie, F.; Qi, Z.; Li, X. Org.
Lett. 2015, 17, 920. (g) Suzuki, C.; Hirano, K.; Satoh, T.; Miura, M. Org.
Lett. 2015, 17, 1597. (h) Zhou, T.; Li, L.; Li, B.; Song, H.; Wang, B. Org.
Lett. 2015, 17, 4204.
Experimental procedure,characterization of new com-
pounds (1H, 13C NMR spectra) and X-ray crystallographic
AUTHOR INFORMATION
Corresponding Author
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We thank the CSIR for funding this project under 12 FYP
ORIGIN Program (CSC0108) and a research fellowship to
R.S.P.
(13) For Cp*Ir(III)-catalyzed metal carbene migratory insertion, see:
(a) Zhang, S.-S.; Jiang, C.-Y.; Wu, J.-Q.; Liu, X.-G.; Li, Q.; Huang, Z.-S.;
Li, D.; Wang, H. Chem. Commun. 2015, 51, 10240. (b) Xia, Y.; Liu, Z.;
Feng, S.; Zhang, Y.; Wang, J. J. Org. Chem. 2015, 80, 223.
(14) (a) Cho, S. H.; Hwang, S. J.; Chang, S. J. Am. Chem. Soc. 2008,
130, 9254. (b) Bering, L.; Antonchick, A. P. Org. Lett. 2015, 17, 3134.
(15) Boekelheide, V.; Linn, W. J. J. Am. Chem. Soc. 1954, 76, 1286.
(16) Aoyagi, Y.; Abe, T.; Ohta, A. Synthesis 1997, 1997, 891.
(17) (a) Li, L.; Brennessel, W. W.; Jones, W. D. J. Am. Chem. Soc. 2008,
130, 12414. (b) Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem.
Soc. 2010, 132, 6908.
(18) Simmons, E. M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51,
3066.
(19) (a) Boutadla, Y.; Davies, D. L.; Jones, R. C.; Singh, K. Chem. - Eur.
J. 2011, 17, 3438. (b) Watanabe, M.; Kashiwame, Y.; Kuwata, S.; Ikariya,
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