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ChemComm
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DOI: 10.1039/C6CC05832A
ARTICLE
Journal Name
Mei, T.-S.; Yu, J.-Q. Nature 2012, 486, 518; (c) Ros, A.; Fernandez,
R.; Lassaletta, J. M. Chem. Soc. Rev. 2014, 43, 3229; (d) Daugulis,
O.; Roane, J.; Tran, L. D. Acc. Chem. Res. 2015, 48, 1053; (e)
Zhang, W.; Zhang, J.; Liu, Y. Youji Huaxue 2014, 34, 36; (f) Phipps,
R. J.; Gaunt, M. J. Science 2009, 323, 1593; (g) Tang, R.-Y.; Li, G.;
Yu, J.-Q. Nature 2014, 507, 215; (h) Frost, C. G.; Paterson, A. J.
ACS Cent. Sci. 2015, 1, 418; (i) Schranck, J.; Tlili, A.; Beller, M.
Angew. Chem., Int. Ed. 2014, 53, 9426.
Conclusions
In summary, an oxidation-induced strategy for para-selective
C-H functionalization was proposed. With this new strategy, a
two- pot method was demonstrated for directly functionalizing
the para-C-H bond of iodobenzene towards the synthesis of
asymmetric diaryl ethers under mild metal-free conditions. In
the meantime, this work provides a general idea for the
development
of
new,
highly
selective
para-C-H
6
7
(a) Wang, X.; Leow, D.; Yu, J. Q. J. Am. Chem. Soc. 2011, 133,
13864; (b) Bag, S.; Patra, T.; Modak, A.; Deb, A.; Maity, S.; Dutta,
U.; Dey, A.; Kancherla, R.; Maji, A.; Hazra, A.; Bera, M.; Maiti, D. J.
Am. Chem. Soc. 2015, 137, 11888.
functionalization
reactions.
Preliminary
mechanistic
investigations indicated that radicals are not involved in this
transformation. Butyric acid could react with iodosobenzene
to form the intermediate A, which is one of key intermediates.
(a) Sibbald, P. A.; Rosewall, C. F.; Swartz, R. D.; Michael, F. E. J.
Am. Chem. Soc. 2009, 131, 15945; (b) Romero, N. A.; Margrey, K.
A.; Tay, N. E.; Nicewicz, D. A. Science 2015, 349, 1326.
The detailed mechanism is currently under investigation in our
laboratory and will be reported in the near future.
8 (a) Metal-Catalyzed Cross-Coupling Reactions; François, D.; Peter
J. S., Ed.; Wiley-VCH Verlag GmbH, 2007; (b) Allard, A.-S.; Neilson,
A. H. In Organic Bromine and Iodine Compounds; Neilson, A. H.,
Ed.; Springer Berlin Heidelberg: Berlin, Heidelberg, 2003, p 1.
Acknowledgements
This work was supported by the 973 Program (2012CB725302), the
National Natural Science Foundation of China (21390400,
21520102003, 21272180, 21302148, and 21372266), the Hubei
Province Natural Science Foundation of China (2013CFA081), the
Research Fund for the Doctoral Program of Higher Education of
China (20120141130002), and the Ministry of Science and
Technology of China (2012YQ120060). The Program of Introducing
Talents of Discipline to Universities of China (111 Program) is also
appreciated.
9
Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255.
10 (a) Zhdankin, V. V.; Protasiewicz, J. D. Coord. Chem. Rev. 2014,
275, 54; (b) Moriarty, R. M. J. Org. Chem. 2005, 70, 2893; (c)
Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221.
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12 Moriarty, R. M.; Duncan, M. P.; Prakash, O. J. Chem. Soc., Perkin
Trans. 1 1987, 1781.
Notes and references
1
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2 (a) Yu, J.-Q.; Ackermann, L.; Shi, Z. C-H activation; Springer:
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Nat. Chem. 2013, 5, 369; (c) Ackermann, L.; Kapdi, A. R.;
Potukuchi, H. K.; Kozhushkov, S. I. In Handbook of Green
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Hartwig, J. F. Acc. Chem. Res. 2012, 45, 864; (e) Bergman, R. G.
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3
(a) Shul'pin, G. B. In Comprehensive Inorganic Chemistry II
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2011, 40, 1857; (d) Engle, K. M.; Yu, J.-Q. J. Org. Chem. 2013, 78,
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2010, 1, 331; (b) Yu, J.-G.; Wang, Z.-H.; Liu, Q.; Chen, X.-Q.; Jiang,
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(a) Wang, X.-C.; Gong, W.; Fang, L.-Z.; Zhu, R.-Y.; Li, S.; Engle
Keary, M.; Yu, J.-Q. Nature 2015, 519, 334; (b) Leow, D.; Li, G.;
4 | J. Name., 2012, 00, 1-3
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