DOI: 10.1039/C4OB02456G
Organic & Biomolecular Chemistry
†
Electronic Supplementary Information (ESI) available: Experimental
11 Reviews: (a) L. H. Jones, N. W. Summerhill, N. A. Swain and J. E.
Mills, Med. Chem. Commun., 2010, 1, 309318; (b) J. Magano and J.
R. Dunetz, Chem. Rev., 2011, 111, 21772250; (c) P. Anbarasan, T.
Schareina and M. Beller, Chem. Soc. Rev., 2011,40, 50495067.
75 12 T. E. Barder, S. D.Walker, J. R. Marinelliand and S. L. Buchwald, J.
Am. Chem. Soc., 2005, 127,46854696.
details, NMR data, Crystallographic data, calculation details are provided.
CCDC 1035363. For ESI and crystallographic data in CIF see DOI:
10.1039/b000000x/.
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5
0
1
(a) R. V. Davies, J. Kennedy, R. W. McIlroy, R. Spence and K. M.
Hill, Nature,1964, 203, 11101115; (b) OECD, Uranium 2009:
Resources, Production and Demand, OECD NEA Publication 6891,
13 H. N. Nguyen, X. Huangand and S. L. Buchwald, J. Am. Chem. Soc.,
2
010, 2932.
2003, 125, 1181811819.
14 All species were fully optimized with B3LYP/(SDD-MWB60: 6-
2
(a) H. J. Schenk, L. Astheimer, E. G. Witte and K. Schwochau, Sep.
Sci. Technol., 1982, 17, 12931308; (b) L. Astheimer, H. J. Schenk, E.
G. Witte and K. Schwochau, Sep. Sci. Technol., 1983, 18, 307339; (c)
N. Seko, A. Katakai, S. Hasegawa, M. Tamada, N. Kasai, H. Takeda,
T. Sugo and K. Saito, Am. Nuc. Soc., 2003, 144, 274278; (d) N. Seko,
M. Tamada, N. Kasai, F. Yoshii and T. Simizu, Proc. Civil Eng.
Ocean, 2004, 20, 611-616; (e) J. Kim, C. Tsouris, R. T. Mayes, Y.
Oyola, T. Saito, C. J. Janke, S. Dai, E. Schneider and D. Sachde, Sep.
Sci. Technol., 2013, 48, 367387.
1
1
2
2
3
3
4
4
5
5
6
6
7
80
311G(d,p)) method on Gaussian 09 suit of program. Frequency
calculation were performed at the same level of theory to ensure all
these structures are local minima. Solution phase single point
calculations were performed with EtOH solvent and SMD model.
More details are given in the supporting information.
85 15 CYLview, 1.0b; C. Y. Legault, Université de Sherbrooke, 2009
1
6 H. Benesi and J. Hildebrand, J. Am. Chem. Soc., 1949, 71, 27032707.
3
4
5
M. J. Manos and M. G. Kanatzidis, J. Am. Chem. Soc., 2012, 134,
1
644116446.
M. Carboni, C. W. Abney, S. Liu and W. Lin, Chem. Sci., 2013, 4,
3962402.
2
L. Zhou, M. Bosscher, C. Zhang, S. Özçubukçu, L. Zhang, W. Zhan, C.
J. Li, J. Liu, M. P. Jensen, L. Lai and C. He, Nat. Chem., 2014, 6,
2
36241.
(a) I. Tabushi,Y. Kobuke and T. Nishiya, Nature,1979, 280, 665666;
b) T. Hirotsu, N. Takagi, S. Katoh, K. Sugasaka, N. Takai, M. Seno
6
(
and T. Tiagaki, Sep. Sci. Technol., 1987, 22, 22172227; (c) T. Kago,
A. Goto, K. Kusakabe and S. Morooka, Ind. Eng. Chem. Res., 1992,
3
1, 204209; (d) A. Zhang, T. Asakura, G. Uchiyama, React. Funct.
Polym., 2003, 57, 6776; (e) P. A. Kavakli, N. Seko, M. Tamada and
O. Güven, Sep. Sci. Technol., 2004, 39, 16311643; (f) S. Das, A. K.
Pandey, A. Athavale, V. Kumar, Y. K. Bhardawaj, S. Sabharwal and
V. K. Manchanda, Desalination, 2008, 232, 243253; (g) T. L. Prasad,
P. K.Tewari and D. Sathiyamoorthy, Ind. Eng.Chem. Res., 2010, 49,
65596565; (h) Y. Yue, R. T. Mayes, J. Kim, P. F. Fulvio, X.-G. Sun,
C. Tsouris, J. Chen, S. Brown and S. Dai, Angew. Chem. Int. Ed., 2013,
5
2, 1345813462; (i) Y. Lu, Nat Chem., 2014, 6, 175177.
7
(a) E. G. Witte, K. S. Schwochau, G. Henkel and B. Krebs, Inorg.
Chim. Acta, 1984, 94, 323331; (b) A. Zhang, T. Asakura and G.
Uchiyama, React. Funct. Polym., 2003, 57, 6776; (c) T. Hirotsu, S.
Katoh and K. Sugasaka, J. Chem. Soc., Dalton Trans. 1986,
1
6091611; (d) Y. Y. Park, S. Y. Kim, J. S. Kim, M. Harada, H.
Tomiyasu, M. Nogami and Y. Ikeda, J. Nucl. Sci. Technol., 2000, 37,
44348; (e) S. Vukovic, L. A. Watson, S. O. Kang, R. Custelcean
3
and B. P. Hay, Inorg. Chem., 2012, 51, 38553859; (f) G. Tian, S.
Teat, Z. Zhang and L. Rao, Dalton. Trans., 2012, 41, 1157911586; (g)
L. Rao, G. Tian, X. Sun, and F. Endrizz, Coordination of UO
2
+
2
with
amidoxime-related ligands: thermodynamics, kinetics, and structure,
Oak Ridge National Laboratory, Oak Ridge, TN, 2013; pp. 20−33; (h)
Cambridge Structural Database, Version 5.32; November 2010; (i) S.
P. Kelley, P. S. Barber, P. H. K. Mullins and R. D. Rogers, Chem.
Commun., 2014, 50, 1250412507.
DFT study investigates the electronic effects of amidoximate ligands
bound to the uranyl cation: C. W. Abney, S. Liu and W. Lin, J. Phys.
Chem. A, 2013, 117, 1155811565.
8
9
(a) N. Sahiner, N. Pekel and O. Guven, React. Funct. Polym., 1999,
3
9, 139146; (b) X. Yang, G. Liu, H. Li, Y. Zhang, D. Song, C. Li, R.
Wang, B. Liu, W. Liang, Y. Jing and G. Zhao, J. Med. Chem., 2010,
3, 10151022; (c) A. ꢀꢁrꢁsꢂ Z. ꢃaꢄn, P. Mizsey, and Z. Finta, Org.
Process Res. Dev., 2012, 16ꢂ 1717−1726.
5
1
0 Examples: (a) T. Schareina, A. Zapf and M. Beller, Chem. Commun.,
2004, 13881389; (b) T. Schareina, A. Zapf and M. Beller, J.
Organomet. Chem., 2004, 689, 45764583; (c) O. Grossman and D.
Gelman, Org. Lett., 2006, 8, 11891191; (d) T. Schareina, R. Jackstell,
T. Schulz, A. Zapf, A. Cotté, M. Gotta and M. Beller, Adv. Synth.
Catal., 2009, 351, 643648; (e) P. Y. Yeung, C. M. So, C. P. Lau and
F. Y. Kwong, Angew. Chem., Int. Ed., 2010, 49, 89188922; (f) P. Y.
Yeung, C. M. So, C. P. Lau and F. Y. Kwong, Org. Lett., 2011, 13,
648651; (g) T. D. Senecal, W. Shu and S. L. Buchwald, Angew.
Chem. Int. Ed., 2013, 52, 1003510039.
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