Catalysis Science & Technology
Paper
10 (a) N. R. Conley, L. A. Labios, D. M. Pearson,
C. C. L. McCrory and R. M. Waymouth, Organometallics,
2007, 26(23), 5447; (b) D. M. Pearson, N. R. Conley and
R. M. Waymouth, Organometallics, 2011, 30, 1445.
11 (a) D. R. Jenson, M. J. Schultz, J. A. Mueller and
M. S. Sigman, Angew. Chem., Int. Ed., 2003, 42(32), 3810; (b)
J. A. Mueller, C. P. Goller and M. S. Sigman, J. Am. Chem.
Soc., 2004, 126, 9724; (c) M. J. Schultz, S. S. Hamilton,
D. R. Jensen and M. S. Sigman, J. Org. Chem., 2005, 70, 3343.
12 D. S. Bailie, G. M. A. Clendenning, L. McNamee and
M. J. Muldoon, Chem. Commun., 2010, 46, 7238.
Acknowledgements
For support we thank the Department of Employment and
Learning, Northern Ireland, Queen's University Belfast Ionic
Liquid Laboratories (QUILL) and the Centre for the Theory
and Application of Catalysis (CenTACat).
References
1 (a) Reviews on Pd(II) catalysed oxidation reactions:
J. Muzart, Tetrahedron, 2003, 59, 5789; (b) S. S. Stahl, Angew.
Chem., Int. Ed., 2004, 43, 3400; (c) C. N. Cornell and
M. S. Sigman, Inorg. Chem., 2007, 46, 1903; (d) X. Chen,
K. M. Engle, D.-H. Wang and J.-Q. Yu, Angew. Chem., Int. Ed.,
2009, 48, 5094; (e) E. M. Beccalli, G. Broggini, M. Martinelli
and S. Sottocornola, Chem. Rev., 2007, 107, 5138; ( f )
K. M. Gligorich and M. S. Sigman, Chem. Commun., 2009,
3854; (g) S. Enthaler and A. Company, Chem. Soc. Rev., 2011,
40, 4912.
2 (a) J. S. Carey, D. Laffan, C. Thomson and M. T. Williams,
Org. Biomol. Chem., 2006, 4, 2337; (b) J. Piera and
J.-E. Bäckvall, Angew. Chem., Int. Ed., 2008, 47, 3506; (c)
Modern Oxidation Methods, ed. J.-E. Bäckvall, Wiley-VCH,
Weinheim, 2nd edn, 2010.
13 C. Melero, O. N. Shishilov, E. Álvarez, P. Palma and
J. Cámpora, Dalton Trans., 2012, 41, 14087.
14 K.-C. Lau, B. J. Pedro, S. Bontemps and R. F. Jordan,
Organometallics, 2013, 32, 6895.
15 (a) H. Jin, K. J. Cavell, B. W. Skelton and A. H. White,
J. Chem. Soc., Dalton Trans., 1995, 2159; (b) J. L. Hoare,
K. J. Cavell, R. Hecker, B. W. Skelton and A. H. White,
J. Chem. Soc., Dalton Trans., 1996, 2197; (c) T. W. Hambley,
K. E. Frankcombe, B. F. Yates, K. J. Cavell and R. B. Knott,
Aust. J. Chem., 2000, 53, 805.
16 (a) B. A. Steinhoff and S. S. Stahl, Org. Lett., 2002, 4(23),
4179; (b) B. A. Steinhoff, S. R. Fix and S. S. Stahl, J. Am.
Chem. Soc., 2002, 124(5), 766; (c) B. A. Steinhoff, I. A. Guzei
and S. S. Stahl, J. Am. Chem. Soc., 2004, 126, 11268; (d)
B. A. Steinhoff and S. S. Stahl, J. Am. Chem. Soc., 2006, 128,
4348; (e) B. A. Steinhoff, A. E. King and S. S. Stahl, J. Org.
Chem., 2006, 71, 1861; ( f ) M. M. Konnick and S. S. Stahl,
J. Am. Chem. Soc., 2008, 130, 5753; (g) B. V. Popp and
S. S. Stahl, Chem. – Eur. J., 2009, 15, 2915.
3 (a) M. S. Sigman and D. R. Jensen, Acc. Chem. Res., 2006, 39,
221; (b) Palladium Catalyzed Oxidation of Hydrocarbons,
ed. P. M. Henry, Kluwer, Boston, 1980; (c) J.-E. Bäckvall,
Acc. Chem. Res., 1983, 16, 335; (d) T. Hosokawa and
S.-I. Murahashi, Acc. Chem. Res., 1990, 23, 49.
4 (a) T. Nishimura, T. Onoue, K. Ohe and S. Uemura, J. Org.
Chem., 1999, 64, 6750; (b) T. Iwasawa, M. Tokunaga, Y. Obora
and Y. Tsuji, J. Am. Chem. Soc., 2004, 126(21), 6554.
5 (a) D. R. Jensen and M. S. Sigman, Org. Lett., 2003, 5(1), 63;
(b) D. R. Jensen, J. S. Pugsley and M. S. Sigman, J. Am. Chem.
Soc., 2001, 123, 7475; (c) J. A. Mueller, D. R. Jensen and
M. S. Sigman, J. Am. Chem. Soc., 2002, 124, 8202; (d)
E. M. Ferreira and B. M. Stoltz, J. Am. Chem. Soc., 2001,
123, 7725.
6 M. J. Schultz, C. C. Park and M. S. Sigman, Chem. Commun.,
2002, 3034.
7 B. P. Buffin, J. P. Clarkson, N. L. Belitz and A. Khundu,
J. Mol. Catal. A: Chem., 2005, 225(1), 111.
17 Review: Q. Cao, L. M. Dornan, L. Rogan, N. L. Hughes and
M. J. Muldoon, Chem. Commun., 2014, 50, 4524.
18 (a) Selected examples of Cu/TEMPO oxidation of primary
alcohols: P. Gamez, I. W. C. E. Arends, J. Reedijk and
R. A. Sheldon, Chem. Commun., 2003, 2414; (b) P. Gamez,
I. W. C. E. Arends, R. A. Sheldon and J. Reedijk, Adv. Synth.
Catal., 2004, 346(7), 805; (c) E. T. T. Kumpulainen and
A. M. P. Koskinen, Chem. – Eur. J., 2009, 15(41), 10901;
(d) J. M. Hoover and S. S. Stahl, J. Am. Chem. Soc., 2011,
133(42), 16901.
19 (a) J. E. Steves and S. S. Stahl, J. Am. Chem. Soc., 2013,
135(42), 15742; (b) Y. Sasano, S. Nagasawa, M. Yamazaki,
M. Shibuya, J. Park and Y. Iwabuchi, Angew. Chem., Int. Ed.,
2014, 53, 3236; (c) L. Rogan, N. L. Hughes, Q. Cao,
L. M. Dornan and M. J. Muldoon, Catal. Sci. Technol., 2014,
4, 1720.
20 (a) M. Molname, P. Mizsey and V. Schröder, J. Hazard.
Mater., 2005, 1, 45; (b) C.-C. Chiang, J.-C. Lee, Y.-M. Change,
C.-F. Chuang and C.-M. Shu, J. Therm. Anal. Calorim.,
2009, 96(3), 759; (c) An Introduction to Fire Dynamics,
ed. D. Drysdale, Wiley, 3rd edn, 2008; (d) E. Brandes and
W. Möller, Safety Characteristic Data: Flammable Liquids and
Gases, Wirtschaftsverlag NW, Bremerhaven, 2008, vol. 1.
21 (a) P. W. N. M. Van Leewen, Appl. Catal., A, 2001, 212, 61;
(b) M. Tromp, J. R. A. Sietsma, J. A. van Bokhoven,
G. P. F. van Strijdonk, R. J. van Haaren, A. M. J. van der Eerden,
8 R. Bortolo, D. Bianchi, R. D'Aloisio, C. Querci and M. Ricci,
J. Mol. Catal. A: Chem., 2000, 153(1), 25.
9 (a) G.-J. ten Brink, I. W. C. E. Arends and R. A. Sheldon,
Science, 2000, 287, 1636; (b) G.-J. ten Brink, I. W. C. E. Arends
and R. A. Sheldon, Adv. Synth. Catal., 2002, 344, 345; (c)
G.-J. ten Brink, I. W. C. E. Arends, M. Hoogenraad, G. Verspui
and R. A. Sheldon, Adv. Synth. Catal., 2003, 345, 497; (d)
G.-J. ten Brink, I. W. C. E. Arends, M. Hoogenraad,
G. Verspui and R. A. Sheldon, Adv. Synth. Catal., 345, 1341;
(e) I. W. C. E. Arends, G.-J. ten Brink and R. A. Sheldon,
J. Mol. Catal. A: Chem., 2006, 251, 246; ( f ) M. Mifsud,
K. V. Parkhomenko, I. W. C. E. Arends and R. A. Sheldon,
Tetrahedron, 2010, 66, 1040.
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