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ChemComm
Page 4 of 4
DOI: 10.1039/C7CC07235J
COMMUNICATION
Journal Name
2908; (n) L. Chen, E. Shi, Z. J. Liu, S. L. Chen, W. Wei, H. Li, K. Xu, X. B.
Wan, Chem. Eur. J. 2011, 17, 4085; (o) Q. Wang, H. Zheng, W. Chai, D. Y.
Chen, X. J. Zeng, R. Z. Fu, R. X. Yuan, Org. Biomol. Chem. 2014, 12, 6549;
product along with regenerating the tert-butyloxy radical. The
observed selectivity of the product in this hydroalkylation reaction
could be attributed to the persistent radical effect.19 The hydrogen
bonding between the oxygen of the carbonyl group and the
hydrogen of the 2,2,2-trifluoroethanol (TFE) or acetic acid possibly
could lower the activation energy of the radical reaction and then
improve the coupling efficiency.20
In conclusion, an iron-catalyzed hydroalkylation of vinylketones
using simple ethers was developed. In this work, both cyclic and
linear simple ethers could couple well with different α- and β-
substituted vinylketones to form multifunctional and complex ether
products in moderate to high yields. Moreover, the availability of
gram-scale synthesis and the ease of transformation of the coupling
products obtained via this protocol to be synthetically useful 1,4-
dicarbonyl and 1,2,5-triol compounds has greatly highlighted
current method in organic synthesis.
(p) Z. Y. Hu, Y. C. Tang, S. Zhang, X. Q. Li, X. H. Du, X. S. Xu, Synlett 2015
,
26, 2557; (q) H. D. Gu, C. Y. Wang, Org. Biomol. Chem. 2015, 13, 5880; (r)
Y. Zheng, J. C. Mao, G. W. Rong, X. F. Xu, Chem. Commun. 2015, 51, 8837;
(s) S. J. Park, J. R. Price, M. H. Todd, J. Org. Chem. 2012, 77, 949.
(a) C. A. Correia, C.-J. Li, Heterocycles. 2010, 82, 555; (b) Y. H. Zhang, C.-J.
Li, Angew. Chem. Int. Ed. 2006, 45, 1949; (c) M.-O. Simon, S. A. Girard, C.-
J. Li, Angew. Chem. Int. Ed. 2012, 51, 7537; (d) Y. H. Zhang, C.-J. Li, J. Am.
Chem. Soc. 2006, 128, 4242; (e) W. Muramatsu, K. Nakano, C.-J. Li, Org.
Lett. 2013, 15, 3650; (f) R.-V. Nguyen, X. Q. Yao, C.-J. Li, Org. Lett. 2006, 8,
2397; (g) R.-V. Nguyen, X. Q. Yao, D. S. Bohle, C.-J. Li, Org. Lett. 2005, 7,
673; (h) C.-J. Li, Acc. Chem. Res. 2009, 42, 335; (i) W. J. Yoo, C. A. Correia,
Y. Zhang, C.-J. Li, Synlett 2009, 138.
7
8
(a) W.-T. Wei, M.-B. Zhou, J.-H. Fan, W. Liu, R.-J. Song, Y. Liu, M. Hu, P.
Xie, J.-H. Li, Angew. Chem. Int. Ed. 2013, 52, 3638; (b) M. Hu, J.-H. Fan, Y.
Liu, X.-H. Ouyang, R.-J. Song, J.-H. Li, Angew. Chem. Int. Ed. 2015, 54,
9577; (c) W.-T. Wei, R.-J. Song, J.-H. Li, Adv. Synth. Catal. 2014, 356,
1703; (d) H.-A. Du, X.-G. Zhang, R.-Y. Tang, J.-H. Li, J. Org. Chem. 2009, 74,
7844; (e) Y. Liang, S. Tang, X.-D. Zhang, L.-Q. Mao, Y.-X. Xie, J.-H. Li, Org.
Lett. 2006, 8, 3017.
We gratefully acknowledge the funding support of the
National Natural Science Foundation of China (21672198,
21372210), the State Key Program of National Natural Science
Foundation of China (21432009) for financial support.
9
(a) Z. L. Meng, S. T. Sun, H. X. Lou, L. Liu, Angew. Chem. Int. Ed. 2014, 53,
543; (b) M. Wan, Z. L. Meng, H. X. Lou, L. Liu, Angew. Chem. Int. Ed. 2014
,
53, 13845; (c) L. Liu, P. E. Floreancig, Angew. Chem. Int. Ed. 2010, 49,
Conflicts of interest
3069; (d) X. Liu, B. Sun, Z. Xie, X. Qin, L. Liu, H. X. Lou, J. Org. Chem. 2013
78, 3104.
,
,
There are no conflicts to declare.
10 (a) J. C. Zhao, W. Zhou, J. L. Han, G. G. Li, Y. Pan, Tetrahedron Lett. 2013
Notes and references
54, 6507; (b) Z. Xie, Y. Cai, H. Hu, C. Lin, J. Jiang, Z. Chen, L. Wang, Y. Pan,
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Mei, J. L. Han, Y. Pan, RSC Adv. 2015, 5, 64961.
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