Dalton Transactions
Paper
lar, complexes bearing the novel BMIMCN ligand, R,R-C4 and 12 A. Murphy, A. Pace and T. D. P. Stack, Org. Lett., 2004,
S,S-C4, were found to be the most active. This highlighted the 6(18), 3119–3122.
stabilising effect that this ligand has on the catalytically active 13 O. Y. Lyakin, R. V. Ottenbacher, K. P. Bryliakov and
species. While high activity was observed for primary alcohol E. P. Talsi, ACS Catal., 2012, 2(6), 1196–1202.
oxidation, acid-mediated over-oxidation and side-reactions 14 R. V. Ottenbacher, D. G. Samsonenko, E. P. Talsi and
proved problematic. In contrast, secondary alcohols had no K. P. Bryliakov, Org. Lett., 2012, 14(17), 4310–4313.
such limitations and could be oxidised to the corresponding 15 M. Papastergiou, P. Stathi, E. R. Milaeva, Y. Deligiannakis
ketones in excellent isolated yields at short reaction times. and M. Louloudi, J. Catal., 2016, 341, 104–115.
Current work in our laboratory is directed toward elucidating 16 K. P. Bryliakov and E. P. Talsi, Coord. Chem. Rev., 2014, 276,
the mechanistic features of the oxidation reaction.
73–96.
17 D. Shen, C. Miao, D. Xu, C. Xia and W. Sun, Org. Lett.,
2015, 17(1), 54–57.
18 A. Berkessel and C. A. Sklorz, Tetrahedron Lett., 1999,
40(45), 7965–7968.
Conflicts of interest
There are no conflicts of interest to declare.
19 K. Nehru, S. J. Kim, I. Y. Kim, M. S. Seo, Y. Kim, S.-J. Kim,
J. Kim and W. Nam, Chem. Commun., 2007, (44), 4623–4625.
20 O. Cusso, I. Garcia-Bosch, D. Font, X. Ribas, J. Lloret-Fillol
and M. Costas, Org. Lett., 2013, 15(24), 6158–6161.
21 J. F. Larrow, E. N. Jacobsen, Y. Gao, Y. Hong, X. Nie and
C. M. Zepp, J. Org. Chem., 1994, 59(7), 1939–1942.
Acknowledgements
The work reported here is supported by the National Research
Foundation of South Africa, Unique Grant No. 99305 and 22 F. Galsbøl, P. Steenbøl and B. S. Sørensen, Acta Chem.
110694, North-West University Unique Grant No. P2A5B1 and Scand., 1972, 26(9), 3605–3611.
an Oppenheimer Memorial Trust Sabbatical Scholarship. Any 23 R. V. Ottenbacher, K. P. Bryliakov and E. P. Talsi, Inorg.
opinion, finding and conclusion or recommendation Chem., 2010, 49(18), 8620–8628.
expressed in this material is that of the author(s) and the NRF 24 SAINT, Version 8.38A, Bruker AXS Inc., 2017.
does not accept any liability in this regard. The infrastructure 25 G. Sheldrick, SADABS, Version 2012/1, Bruker AXS Inc.,
support provided by the Focus Area for Chemical Resource
2012.
Beneficiation (CRB) and in particular the Catalysis and 26 APEX3, Version 2017.3, Bruker AXS Inc., 2017.
Synthesis Research Group and Laboratory for Analytical 27 G. Sheldrick, Acta Crystallogr., Sect. C: Struct. Chem., 2015,
Services (LAS), at the NWU, is gratefully acknowledged. SASOL
71(1), 3–8.
postgraduate bursary support to VV is gratefully acknowledged. 28 L. J. Barbour, J. Supramol. Chem., 2001, 1(4), 189–191.
29 J. L. Atwood and L. J. Barbour, Cryst. Growth Des., 2003,
3(1), 3–8.
30 R. Gopalan, Inorganic chemistry for undergraduates,
References
Universities Press, Hyderabad, India, 2009.
1 Z. P. Ye, Z. H. Fu, S. Zhong, F. Xie, X. P. Zhou, F. L. Liu and 31 L. Gómez, I. Garcia-Bosch, A. Company, X. Sala,
D. L. Yin, J. Catal., 2009, 261(1), 110–115.
2 A. D. Fortineau, J. Chem. Educ., 2004, 81(1), 45–50.
X. Fontrodona, X. Ribas and M. Costas, Dalton Trans., 2007,
(47), 5539–5545.
3 I. Kani and S. Bolat, Appl. Organomet. Chem., 2016, 30(8), 32 M. Wu, B. Wang, S. Wang, C. Xia and W. Sun, Org. Lett.,
713–721. 2009, 11(16), 3622–3625.
4 N. J. Hill, J. M. Hoover and S. S. Stahl, J. Chem. Educ., 2013, 33 C. Miao, B. Wang, Y. Wang, C. Xia, Y.-M. Lee, W. Nam and
90(1), 102–105. W. Sun, J. Am. Chem. Soc., 2016, 138(3), 936–943.
5 J. Ni, W. J. Yu, L. He, H. Sun, Y. Cao, H. Y. He and 34 J. Glerup, P. A. Goodson, A. Hazell, R. Hazell, D. J. Hodgson,
K. N. Fan, Green Chem., 2009, 11(6), 756–759.
6 R. Anderson, K. Griffin, P. Johnston and P. L. Alsters, Adv.
Synth. Catal., 2003, 345(4), 517–523.
7 I. Garcia-Bosch, X. Ribas and M. Costas, Adv. Synth. Catal.,
2009, 351(3), 348–352.
C. J. McKenzie, K. Michelsen, U. Rychlewska and
H. Toftlund, Inorg. Chem., 1994, 33(18), 4105–4111.
35 M. F. Reynolds, M. Costas, M. Ito, D.-H. Jo, A. A. Tipton,
A. K. Whiting and L. Que, J. Biol. Inorg. Chem., 2003, 8(3),
263–272.
8 I. Garcia-Bosch, A. Company, X. Fontrodona, X. Ribas and 36 K. Chen, M. Costas and J. L. Que, J. Chem. Soc., Dalton
M. Costas, Org. Lett., 2008, 10(11), 2095–2098. Trans., 2002, (5), 672–679.
9 D. Shen, C. Miao, S. Wang, C. Xia and W. Sun, Org. Lett., 37 M. Lokov, S. Tshepelevitsh, A. Heering, P. G. Plieger,
2014, 16(4), 1108–1111.
10 A. Murphy, G. Dubois and T. D. P. Stack, J. Am. Chem. Soc.,
2003, 125(18), 5250–5251.
11 R. V. Ottenbacher, D. G. Samsonenko, E. P. Talsi and
K. P. Bryliakov, ACS Catal., 2014, 4(5), 1599–1606.
R. Vianello and I. Leito, Eur. J. Org. Chem., 2017, (30),
4475–4489.
38 J. W. De Boer, W. R. Browne, J. Brinksma, P. L. Alsters,
R. Hage and B. L. Feringa, Inorg. Chem., 2007, 46(16),
6353–6372.
This journal is © The Royal Society of Chemistry 2018
Dalton Trans., 2018, 47, 16534–16542 | 16541