Organic & Biomolecular Chemistry
Paper
Fueyo, T. Noël, I. W. C. E. Arends and F. Hollmann,
Beilstein J. Org. Chem., 2018, 14, 697; (d) G. Wu, G. L. Brett,
A. Constantinou, P. Ellis, S. Kuhn, G. J. Hutchings,
D. Bethell and A. Gavriilidis, Catal. Sci. Technol., 2016, 6,
4749; (e) M. Morad, M. Sankar, E. Cao, E. Nowicka,
T. E. Davies, P. J. Miedziak, D. J. Morgan, D. W. Knight,
D. Bethell, A. Gavriilidis and G. J. Hutchings, Catal. Sci.
Technol., 2014, 4, 3120.
8 (a) T. Matsumoto, M. Ueno, N. Wang and S. Kobayashi,
Chem. – Asian J., 2008, 3, 196; (b) R. Anderson, K. Griffin,
P. Johnston and P. L. Alsters, Adv. Synth. Catal., 2003, 345,
517.
9 (a) Y. Kon, Y. Usui and K. Sato, Chem. Commun., 2007,
4399; (b) Y. Kon, H. Yazawa, Y. Usui and K. Sato, Chem. –
Asian J., 2008, 3, 1642.
10 R. Javaid, D. A. P. Tanaka, H. Kawanami and T. M. Suzuki,
Chem. Lett., 2009, 38, 146.
Acknowledgements
This article is based on results obtained from a project,
JPNP19004, subsidized by the New Energy and Industrial
Technology Development Organization (NEDO), Japan.
Notes and references
1 (a) R. C. Larock, Comprehensive organic transformations,
JohnWiley & Sons, Inc., 2nd edn, 1999, 1646; (b) J. March,
March’s Advanced Organic Chemistry, JohnWiley & Sons,
Inc., New York, 5th edn, 2007, 1715; (c) G. Franz and
R. A. Sheldon, Ullmann’s encyclopedia of industrial chem-
istry, VCH, 5th edn, 1991, vol. A18, p. 261; (d) S. Caron,
R. W. Dugger, S. G. Ruggeri, J. A. Ragan and D. H. B. Ripin,
Chem. Rev., 2006, 106, 2943.
2 (a) D. B. Dess and J. C. Martin, J. Org. Chem., 1983, 48,
4155; (b) D. B. Dess and J. C. Martin, J. Am. Chem. Soc.,
1991, 113, 7277.
11 Y. Nagai, T. Hirabayashi, K. Dohmae, N. Takagi,
T. Minami, H. Shinjoh and S. Matsumoto, J. Catal., 2006,
242, 103.
3 (a) B. M. Trost, Science, 1991, 254, 1471; (b) R. A. Sheldon,
Chem. Ind., 1992, 903.
12 The turnover frequency (TOF) per Pt black was defined as
[mole of generated 2]/[mole of Pt in column reactor].
13 Aerobic oxidation using a Cu-based catalytic system is
effective for highly selective oxidation of aliphatic alcohols;
for selected examples, see: (a) M. F. Semmelhack,
C. R. Schmid, D. A. Cortés and C. S. Chou, J. Am. Chem.
Soc., 1984, 106, 3374; (b) I. E. Markó, P. R. Giles,
M. Tsukazaki, S. M. Brown and C. J. Urch, Science, 1996,
274, 2044; (c) P. Gamez, I. W. C. E. Arends, J. Reedijk and
R. A. Sheldon, Chem. Commun., 2003, 2414; (d) J. M. Hoover
and S. S. Stahl, J. Am. Chem. Soc., 2011, 133, 16901.
However, to the best of our knowledge, there are no
examples to apply the systems to continuous flow reactors
in the presence of environmentally friendly oxidants such
as O2 and H2O2.
4 I. W. C. E. Arends and R. A. Sheldon, Modern oxidation of
alcohols using environmentally benign oxidants, in
modern oxidation methods, WILEY-VCH, 2004, 83.
5 (a) K. Masuda, T. Ichitsuka, N. Koumura, K. Sato and
S. Kobayashi, Tetrahedron, 2018, 74, 1705; (b) B. Gutmann,
D. Cantillo and C. O. Kappe, Angew. Chem., Int. Ed., 2015,
54, 6688; (c) H. P. L. Gemoets, Y. Su, M. Shang, V. Hessel,
R. Luque and T. Noël, Chem. Soc. Rev., 2016, 45, 83.
6 Recent examples about environmentally benign flow oxi-
dation of alcohols, see: (a) L. J. Durndell, C. Cucuzzella,
C. M. A. Parlett, M. A. Isaacs, K. Wilson and A. F. Lee,
Catal. Today, 2019, 333, 161; (b) M. Santonastaso,
S. J. Freakley, P. J. Miedziak, G. L. Brett, J. K. Edwards and
G. J. Hutchings, Org. Process Res. Dev., 2014, 18, 1455;
(c) D. S. Mannel, S. S. Stahl and T. W. Root, Org. Process
Res. Dev., 2014, 18, 1503; (d) G. Wu, E. Cao, P. Ellis,
A. Constantinou, S. Kuhn and A. Gavriilidis, Chem. Eng. J.,
2019, 377, 120086; (e) W. Gao, L. Du, W. Jiao and Y. Liu,
Chin. J. Chem. Eng., 2020, 28, 808; (f) M. Burkholder,
S. E. Gilliland III, A. Luxon, C. Tang and B. F. Gupton,
Catalysts, 2019, 9, 95; (g) C. Liu, Z. Fang, Z. Yang, Q. Li,
S. Guo, K. Zhang, P. Ouyang and K. Guo, Tetrahedron Lett.,
2015, 56, 5973; (h) M. Peer, N. Weeranoppanant, A. Adamo,
Y. Zhang and K. F. Jensen, Org. Process Res. Dev., 2016, 20,
1677.
14 (a) C. D. Wagner, W. M. Riggs, L. E. Davis and
J. F. Moulder, Handbook of X-ray photoelectron spectroscopy,
ed. G. E. Mullemberg, PerkinElmer, Eden Prairie, MN,
1978; (b) Y. Yamauchi, T. Ohsuna and K. Kuroda, Chem.
Mater., 2007, 19, 1335.
15 V. Voorhees and R. Adams, J. Am. Chem. Soc., 1922, 44,
1397.
16 (a) SDBSWeb: https://sdbs.db.aist.go.jp (National Institute
of Advanced Industrial Science and Technology, Dec. 8,
2020); (b) C. J. Pouchert and J. Behnke, The Aldrich Library
of 13C and 1H FT NMR Spectra, Aldrich Chemical,
Milwaukee, 1st edn, 1993, vol. 2, 930; (c) C. J. Pouchert and
J. Behnke, The Aldrich Library of 13C and 1H FT NMR
Spectra, Aldrich Chemical, Milwaukee, 1st edn, 1993, vol. 1,
743; (d) C. J. Pouchert and J. Behnke, The Aldrich Library of
7 (a) S. R. Chaudhuri, J. Hartwig, L. Kupracz, T. Kodanek,
J. Wegner and A. Kirschning, Adv. Synth. Catal., 2014, 356,
3530; (b) B. Sarmah, B. Satpati and R. Srivastava, ACS
Omega, 2018, 3, 7944; (c) M. M. C. H. van Schire,
T. P. de Almeida, G. Laudadio, F. Tieves, E. Fernández-
1
13C and H FT NMR Spectra, Aldrich Chemical, Milwaukee,
1st edn, 1993, vol. 2, 940.
This journal is © The Royal Society of Chemistry 2021
Org. Biomol. Chem., 2021, 19, 1115–1121 | 1121