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COMMUNICATION
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DOI: 10.1039/C9CC03939B
Angew. Chem. Int. Ed. 2015, 54, 1261-1265.
bonds to prepare the corresponding ketones with an inorganic-ligand
interaction between the bromide ion and iron complex via multiple
hydrogen bonds to form a supramolecular compound (FeMo6∙2Br)
could activate the C-H bonds of the methylene group to easily
prepare the ketones. The study of the substrate scope shows that
both activated and un-activated aliphatic C-H bonds (41 examples)
compounds, including natural scaffolds such as 1β-hydroxy
alantolactone and dihydro-β-agarofuran, have been converted into
the corresponding ketones with high selectivity and good to excellent
iron catalyst is stable and recyclable, and can be easily prepared by a
simple one-step synthesis from simple inorganic metal salts.
Importantly, the effect of bromide ion could provide valuable
information for the further design of additives for selective iron-
catalyzed direct oxidation and functionalization reactions of C(sp3)-H
bonds.
a) D. P. Hruszkewycz, K. C. Miles, O. R. Thiel, S. S. Stahl, Chem.
Sci. 2017, 8, 1282-1287; b) N. Sauermann, T. Meyer, C. Tian, L.
Ackermann, J. Am. Chem. Soc. 2017, 139, 18452–18455.
G. Olivo, G. Farinelli, A. Barbieri, O. Lanzalunga, S. Di Stefano,
M. Costas, Angew. Chem. Int. Ed. 2017, 56, 16347-16351.
E. M. Simmons, J. F. Hartwig, Nature 2012, 483, 70–73.
a) S. Li, B. Zhu, R. Lee, B. Qiao, Z. Jiang, Org. Chem. Front. 2018,
5, 380-385; b) D. P. Hruszkewycz, K. C. Miles, O. R. Thiel, S. S.
Stahl, Chem. Sci. 2017, 8, 1282-1287.
a) W. Zhang, B. O. Burek, E. Fernàndez-Fueyo, M. Alcalde, J. Z.
Bloh, F. Hollmann, Angew. Chem. Int. Ed. 2017, 56, 15451-
15455; b) D. Holtmann, M. W. Fraaije, I. W. C. E. Arends, D. J.
Opperman, F. Hollmann, Chem. Commun. 2014, 50, 13180–
13200; c) E. Churakova, M. Kluge, R. Ullrich, I. Arends, M.
Hofrichter, F. Hollmann, Angew. Chem. Int. Ed. 2011, 50,
10716-10719.
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9
This work is supported by the National Natural Science
Foundation of China (Nos. 21871183, 21631007, 21225103),
10 a) C.L. Hill, & Prosser- C.M. McCartha, Coord. Chem. Rev. 1995,
143, 407-455; b) N. Mizuno, C. Nozaki, I. Kiyoto, & M. Misono,
J. Am. Chem. Soc. 1998, 120, 9267-9272; c) R. Neumann, & C.
Abu-Gnim, J. Chem. Soc., Chem. Commun. 1989, 18, 1324-1325;
d) N. Mizuno, K. Kamata, Coord. Chem. Rev. 2011, 255, 2358-
2370; e) A. Mꢀller, P. Kꢁgerler, A. W. M. Dress, Coord. Chem.
Rev. 2001, 222, 193-218;f) M. T. Pope, A. Mꢀller, Angew. Chem.
Int. Ed. 1991, 30, 34.
Doctoral Fund of Ministry of
Education of China
No.
20130002110042, Tsinghua University Initiative Foundation
Research Program No. 20131089204 and the State Key Laboratory of
Natural and Biomimetic Drugs K20160202. The start-up fund of
Shanghai Institute of Technology is also gratefully acknowledged.
Conflicts of interest
11 a) Y. Kikukawa, K. Yamaguchi, N. Mizuno, Angew. Chem. Int. Ed.
2010, 49, 6096-6100; b) R. Ben-Daniel, P. Alsters, R. Neumann,
J. Org. Chem. 2001, 66, 8650-8653; c) I. A. Weinstock, E. M. G.
Barbuzzi, M. W. Wemple, J. J. Cowan, R. S. Reiner, D. M. Sonnen,
R. A. Heintz, J. S. Bond, C. L. Hill, Nature 2001, 414, 191-195.
12 a) Y. Liu, S.-F. Zhao, S.-X. Guo, A. M. Bond, J. Zhang, J. Am. Chem.
Soc. 2016, 138, 2617-2628; b) S. S. Wang, G. Y. Yang, Chem. Rev.
2015, 115, 4893–4962; c) B. B. Sarma, I. Efremenko, R.
Neumann, J. Am. Chem. Soc. 2015, 137, 5916−5922; d) C. Zou,
Z. Zhang, X. Xu, Q. Gong, J. Li, C. Wu, J. Am. Chem. Soc. 2012,
134, 87−90; e) K. Kamata, K. Yonehara, Y. Nakagawa, K. Uehara,
N. Mizuno, Nat. Chem. 2010, 2, 478-483.
In There are no conflicts to declare.
Notes and references
1
a) R. R. Karimov, J. F. Hartwig, Angew. Chem. Int. Ed. 2018, 57,
4234–4241; b) T. Gensch, M. N. Hopkinson, F. Glorius. Wencel-
Delord, Chem. Soc. Rev. 2016, 45, 2900-2936; c) S. E. Allen, R.
R. Walvoord, R. Padilla-Salinas, M. C. Kozlowski, Chem. Rev.
2013, 113, 6234–6458; d) Z. Shi, C. Zhang, C. Tang, N. Jiao,
Chem. Soc. Rev. 2012, 41, 3381–3430; e) A. N. Campbell, S. S.
Stahl, Acc. Chem. Res. 2012, 45, 851–863; f) C. Liu, H. Zhang, W.
Shi, A. Lei, Chem. Rev. 2011, 111, 1780–1824; g) T.
Punniyamurthy, S. Velusamy, J. Iqbal, Chem. Rev. 2005, 105,
2329–2364.
13 a) Jr. H. T. Evans, J. Am. Chem. Soc. 1948, 70, 1291-1292; (b) J.
S. Anderson, Nature 1937, 140, 850.
14 a) H. Yu, Z. Wu, Z. Wei, Y. Zhai, S. Ru, Q. Zhao, J. Wang, S. Han,
Y. Wei, Commun. Chem. 2019, doi.org/10.1038/s42004-019-
0109-4; b) M. Zhang, Y. Zhai, S. Ru, D. Zang, S. Han, H. Yu, Y.
Wei, Chem. Commun. 2018, 54, 10164-10167; c) H. Yu, S. Ru, G.
Y. Dai, Y. Y. Zhai, H. L. Lin, S. Han, Y. G. Wei, Angew. Chem. Int.
Ed. 2017, 56, 3867-3871; d) H. Yu, Y. Zhai, G. Dai, S. Ru, S. Han,
Y. Wei, Chem. - Eur. J. 2017, 23, 13883-13887.
2
a) T. Nanjo, E. C. De Lucca, M. C. White, J. Am. Chem. Soc. 2017,
139, 14586–14591; b) B. Chandra, K. K. Singh, S. Sen Gupta,
Chem. Sci. 2017, 8, 7545–7551; c) B. Chandra, K. K. Singh, S. S.
Gupta, Chem. Sci. 2017, 8, 7545–7551; d) S. E. Ammann, W. Liu,
M. C. White, Angew. Chem. Int. Ed. 2016, 55, 9571–9575; e) B.
Műhldorf, R. Wolf, Angew .Chem. Int. Ed. 2016, 55, 427–430; f)
A. Al-hunaiti, M. Räisänen, T. Repo, Chem. Commun. 2016, 52,
2043-2046; g) P. E. Gormisky, M. C. White, J. Am. Chem. Soc.
2013, 135, 14052–14055; h) M. S. Chen, M. C. White, Science
2010, 327, 566−571; i) M. S. Chen, M. C. White, Science 2007,
318, 783–787.
15 L. Ren, L. Wang, Y. Lv, S. Shang, B. Chen, S. Gao, Green Chem.
2015, 17, 2369-2372.
16 Y. Zhai, M. Zhang, H. Fang, S. Ru, H. Yu, W. Zhao, Y. Wei, Org.
Chem. Front., 2018, 5, 3454-3459.
3
a) J. N. Jaworski, S. D. McCann, I. A. Guzei, S. S. Stahl, Angew.
Chem. Int. Ed. 2017, 56, 3605-3610; b) L. V. Desai, K. L. Hull, M.
S. Sanford, J. Am. Chem. Soc. 2004, 126, 9542-9543.
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