Chemistry - A European Journal
10.1002/chem.201901803
FULL PAPER
compound was determined by comparing the normalized peak area with
the one obtained for benzyl alcohol, from which corresponding carbon
yields were obtained by dividing the number of mmoles of C in the
respective product by the total mmoles of C initially supplied in the
substrate (i.e. 4 mmol). Finally, quantitative Fourier Transform Infrared
[18] E. Roduner, W. Kaim, B. Sarkar, V. B. Urlacher, J. Pleiss, R. Gläser, W.-
D. Einicke, G. A. Sprenger, U. Beifuß, E. Klemm, C. Liebner, H.
Hieronymus, S.-F. Hsu, B. Plietker, S. Laschat, ChemCatChem 2013, 5,
82−112.
[19] J. A. Labinger, Chem. Rev. 2017, 117, 8483−8496.
[20] N. F. Gol’dshlger, V. V. Lavrushko, A. P. Khrushch, A. A. Shteinman, Izv.
Akad. Nauk SSSR, Ser. Khim. 1976, 2174−2178.
(FTIR) spectroscopy was conducted, using a Gasmet DX4000 FTIR gas
analyzer, to evaluate the presence of gaseous products in the vapor phase.
Prior to each measurement, part of the vapor phase was transferred from
[21] M. Lin, C. Shen, E. A. Garcia-Zayas, A. Sen, J. Am. Chem. Soc. 2001,
123, 1000−1001.
the reactor into a plastic syringe (5 mL) and injected as such into a N
2
stream (160 mL/min). Next, volume concentrations of the various
compounds were measured at the detector level and were processed
using the Calcmet Standard software version 12.161.
[22] D. R. Weinberg, J. A. Labinger, J. E. Bercaw, Organometallics 2007, 26,
167−172.
[23] Y. V. Geletii, A. E. Shilov, Kinet. Katal. 1983, 24, 486−489.
[
[
[
24] M. S. Freund, J. A. Labinger, N. S. Lewis, J. E. Bercaw, J. Mol. Catal.
994, 87, L11−L15.
25] I. Bar-Nahum, A. M. Khenkin, R. Neumann, J. Am. Chem. Soc. 2004,
26, 10236−10237.
1
Acknowledgements
1
26] (a) D. M. Robinson, G. M. Keating, CNS Drugs 2007, 21, 337−354.
(b) W. Schwarz, J. Schossig, R. Rossbacher, H. Höke in Ullmann’s
encyclopedia of industrial chemistry, Vol. 6, Wiley-VCH, Weinheim, 2000,
pp. 457−463. (c) K. Miltenberger in Ullmann’s encyclopedia of industrial
chemistry, Vol. 18, Wiley-VCH, Weinheim, 2000, pp. 481−492.
27] P. Atkins, T. Overton, J. Rourke, M. Weller, F. Armstrong, M. Hagerman
in Inorganic chemistry, W. H. Freeman and Company, New York, 2010,
pp. 787−799.
M.J. thanks the Fonds Wetenschappelijk Onderzoek (FWO), the
Agency for Innovation by Science and Technology (IWT) and the
Industrial Research Fund (IOF) of KU Leuven for funding. D.E.D.V.
acknowledges the IWT and FWO for research project funding, the
Flemish government for long-term structural funding through
Methusalem, and Belspo (IAP-PAI 7/05) for financial support. The
authors also thank Karel Deurinckx for his assistance throughout
the NMR measurements and Sabina Accardo for her support
during FTIR analysis of the vapor phase.
[
[28] C. Shen, E. A. Garcia-Zayas, A. Sen, J. Am. Chem. Soc. 2000, 122,
4029−4031.
[
[
29] J. H. Lee, K. S. Yoo, K. W. Jung, Bull. Korean Chem. Soc. 2011, 32,
881−2882.
2
30] R. J. Lemire, U. Berner, C. Musikas, D. A. Palmer, P. Taylor, O.
Tochiyama in Chemical thermodynamics of iron part 1, Vol. 13a (Ed.:
OECD Nuclear Energy Agency Data Bank), OECD Publications, Paris,
Keywords: CH activation • Hydroxylation • Molecular oxygen •
Primary CH bonds • Shilov-type Pt catalysis
2013, pp. 234−282.
[
[
1]
2]
S. S. Stahl, J. A. Labinger, J. E. Bercaw, Angew. Chem., Int. Ed. 1998,
7, 2180−2192.
[31] (a) J. M. Casas, G. Crisóstomo, L. Cifuentes, Hydrometallurgy 2005, 80,
254−264. (b) G. Yue, L. Zhao, O. G. Olvera, E. Asselin, Hydrometallurgy
2014, 147−148, 196−209.
3
(a) J. F. Hartwig, M. A. Larsen, ACS Cent. Sci. 2016, 2, 281−292. (b) V.
Dantignana, M. Milan, O. Cussó, A. Company, M. Bietti, M. Costas, ACS
Cent. Sci. 2017, 3, 1350−1358.
[32] S.-I. Ohira, Y. Hiroyama, K. Nakamura, T. Koda, P. K. Dasgupta, K.
Toda, Talanta 2015, 132, 228−233.
[
3]
J. A. Labinger in Alkane CH activation by single-site metal catalysis,
Vol. 39 (Ed.: P. J. Pérez), Springer, Dordrecht, 2012, pp. 17−72.
J. A. Labinger, J. E. Bercaw, Nature 2002, 417, 507−514.
K. Noweck, W. Grafahrend in Ullmann’s encyclopedia of industrial
chemistry, Vol. 14, Wiley-VCH, Weinheim, 2006, pp. 117−142.
X. Tang, X. Jia, Z. Huang, Chem. Sci. 2018, 9, 288−299.
[33] (a) A. S. Jhaveri, M. M. Sharma, Chem. Eng. Sci. 1967, 22, 1−6. (b) J. A.
Keith, J. Oxgaard, W. A. Goddard, J. Am. Chem. Soc. 2006, 128,
3132−3133. (c) J. J. Dong, W. R. Browne, B. L. Feringa, Angew. Chem.,
Int. Ed. 2015, 54, 734−744.
[
[
4]
5]
[34] G. A. Truesdale, A. L. Downing, Nature 1954, 173, 1236.
[35] R. A. Periana, D. J. Taube, S. Gamble, H. Taube, T. Satoh, H. Fuhii,
Science 1998, 280, 560−564.
[
[
[
6]
7[
8]
A. E. Shilov, G. B. Shul’pin, Chem. Rev. 1997, 97, 2879−2932.
F. Roudesly, J. Oble, G. Poli, J. Mol. Catal. A: Chem. 2017, 426,
[36] R. Palkovits, C. von Malotki, M. Baumgarten, K. Müllen, C. Baltes, M.
Antonietti, P. Kuhn, J. Weber, A. Thomas, F. Schüth, ChemSusChem
2010, 3, 277−282.
275−296.
[
[
[
[
9]
A. Sen, Acc. Chem. Res. 1998, 31, 550−557.
10] E. G. Chepaikin, Russ. Chem. Rev. 2011, 80, 363−396.
11] J. L. Garnett, R. J. Hodges, J. Am. Chem. Soc. 1967, 89, 4546−4547.
12] (a) N. F. Gol’dshlger, M. B. Tyabin, A. E. Shilov, A. A. Shteinman, Zh.
Fiz. Khim. 1969, 43, 2174. (b) N. F. Gol’dshlger, V. V. Eskova, A. E.
Shilov, A. A. Shteinman, Zh. Fiz. Khim. 1972, 46, 1353−1354.
[37] S. R. Maqsood, N. Islam, S. Bashir, B. Khan, A. H. Pandith, J. Coord.
Chem. 2013, 66, 2308−2315.
[38] U. Izawa, S. S. Stahl, Adv. Synth. Catal. 2010, 352, 3223−3229.
[39] M. B. Smith, J. March in March’s advanced organic chemistry: reactions,
mechanisms and structure, Vol. 6, John Wiley & Sons, Inc., New Jersey,
2007, pp. 408.
[
[
[
13] (a) A. A. Shteinman, J. Organomet. Chem. 2015, 793, 34−40. (b) A. A.
Shteinman, J. Mol. Catal. A: Chem. 2017, 426, 305−315.
[40] J. M. Rawson, R. E. P. Winpenny, Coord. Chem. Rev. 1995, 139,
313−374.
14] G. A. Luinstra, L. Wang, S. S. Stahl, J. A. Labinger, J. E. Bercaw, J.
Organomet. Chem. 1995, 504, 75−91.
[41] A. Z. Michelson, A. Petronico, J. K. Lee, J. Org. Chem. 2012, 77,
1623−1631.
15] (a) L.-C. Kao, A. Sen, J. Chem. Soc., Chem. Commun. 1991, 0,
1
242−1243. (b) A. Sen, M. Lin, L.-C. Kao, A. C. Hutson, J. Am. Chem.
Soc. 1992, 114, 6385−6392. (c) N. Basickes, A. Sen, Polyhedron 1995,
4, 197−202. (d) A. C. Hutson, M. Lin, N. Basickes, A. Sen, J. Organomet.
[42] L. R. Holloway, L. Li in Nitrosyl complexes in inorganic chemistry,
biochemistry and medicine II (Ed.: D. M. P. Michael), Springer, Berlin,
2012, pp. 53−98.
1
Chem. 1995, 504, 69−74.
[43] T. J. Ferris, M. J. Went, Forensic Sci. Int. 2012, 216, 158−162.
[44] T. Mallat, A. Baiker, Catal. Today 1994, 19, 247−284.
[45] J. H. Teles, I. Hermans, G. Franz, R. A. Sheldon in Ullmann’s
encyclopedia of industrial chemistry, Wiley-VCH, Weinheim, 2015,
pp. 1−102.
[
[
16] M. Lee, M. S. Sanford, J. Am. Chem. Soc. 2015, 137, 12796−12799.
17] B. D. Dangel, J. A. Johnson, D. Sames, J. Am. Chem. Soc. 2001, 123,
8149−8150.
This article is protected by copyright. All rights reserved.