ACS Catalysis
chemical moieties, including halides, nitriles, and
Page 6 of 7
F.; Bruschi, M.; Rindone, B., Reaction Products and
Mechanism of the Regioselective Oxidation of N-
Phenylmorpholine by Ozone. Tetrahedron 2012, 68,
8267-8275.
3. Binder, C. M.; Dixon, D. D.; Almaraz, E.; Tius, M. A.;
Singaram, B., A Simple Procedure for C-C Bond Cleavage
of Aromatic and Aliphatic Epoxides with Aqueous
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carbonyl substrates. Importantly, this protocol has
proven effective for the late-stage functionalization of
the drug linezolid, with other functional groups
remaining untouched.
AUTHOR INFORMATION
Sodium
Periodate
Under
Ambient
Conditions.
Corresponding Author
Tetrahedron lett. 2008, 49, 2764-2767.
*
Matthias Beller: matthias.beller@catalysis.de
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. Malaprade, L., Bull. Soc. Chim. Fr. 1934, 3, 833.
. Criegee, R., Eine Oxydative Spaltung von Glykolen.
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ORCID
Berichte der Dtsch. Chem. Gesellschaft 1931, 64, 260-266.
6. Straganz, G. D.; Glieder, A.; Brecker, L.; Ribbons, D.
W.; Steiner, W., Acetylacetone-Cleaving Enzyme Dke1: A
Novel C-C-Bond-Cleaving Enzyme from Acinetobacter
johnsonii. Biochem. J. 2003, 369, 573-581.
David K. Leonard: 0000-0002-3471-2060
Wu Li: 0000-0001-7102-4630
Kathrin Junge: 0000-0001-7044-8888
Matthias Beller: 0000-0001-5709-0965
Author Contributions
7. Peck, S. C.; Cooke, H. A.; Cicchillo, R. M.; Malova, P.;
Hammerschmidt, F.; Nair, S. K.; van der Donk, W. A.,
Mechanism and Substrate Recognition of 2-
Hydroxyethylphosphonate Dioxygenase. Biochemistry
All authors have given approval to the final version of the
manuscript. M.B., K.J., D.K.L., and W.L. conceived and
designed the experiments; D.K.L and W.L. performed all
catalytic oxidation experiments and analyzed the data;
D.K.L., K.J., and M.B. co-wrote the paper.
2011, 50, 6598-6605.
8. Keegan, R.; Lebedev, A.; Erskine, P.; Guo, J.; Wood, S.
P.; Hopper, D. J.; Rigby, S. E. J.; Cooper, J. B., Structure of
the 2,4′-Dihydroxyacetophenone Dioxygenase from
Alcaligenes sp. 4HAP. Acta. Cryst. 2014, 70, 2444-2454.
Notes
The authors declare no competing financial interest.
9. Roque, J. B. K., Y.; Göttemann, L. T.; Sarpong, R. ,
Deconstructive Fluorination of Cyclic Amines by Carbon-
Carbon Cleavage. Science 2018, 361, 171-174.
ASSOCIATED CONTENT
Supporting
Information.
Experimental
procedures;
10. Zhou, Z. Z.; Liu, M.; Lv, L.; Li, C. J., Silver(I)-Catalyzed
characterization data for compounds prepared. This material
is available free of charge via the Internet at
http://pubs.acs.org.
Widely Applicable Aerobic 1,2-Diol Oxidative Cleavage.
Angew. Chem., Int. Ed. 2018, 57, 2616-2620.
11. Li, W.; Liu, W.; Leonard, D. K.; Rabeah, J.; Junge, K.;
Brückner, J.; Beller, M., Practical Catalytic Cleavage of
C(sp³)–C(sp³) Bonds in Amines. Angew. Chem., Int. Ed.
2019, 131, 10803-10807.
12. He, K.; Zhang, T.; Zhang, S.; Sun, Z.; Zhang, Y.; Yuan,
Y.; Jia, X., Tunable Functionalization of Saturated C-C and
C-H Bonds of N,N'-Diarylpiperazines Enabled by tert-
ACKNOWLEDGMENTS
We gratefully acknowledge the support from the Federal
Ministry of Education and Research (BMBF) and the State of
Mecklenburg-Vorpommern. Financial support by Fonds der
Chemischen Industrie (Kekulé-Stipendium n. 103231) for
D.K.L. is also acknowledged. We thank the analytical staff of
the Leibniz-Institute for Catalysis, Rostock for their excellent
service.
Butyl Nitrite (TBN) and NaNO
1, 5030-5034.
3. Tomas, R. A.; Bordado, J. C.; Gomes, J. F., p-Xylene
Oxidation to Terephthalic Acid: A Literature Review
Oriented Toward Process Optimization and
Development. Chem. Rev. 2013, 113, 7421-69.
2
Systems. Org. Lett. 2019,
2
1
ABBREVIATIONS
TBN, tert-butyl nitrite; p-NBA, para-nitrobenzoic acid;
TEMPO, (2,2,6,6-tetramethylpiperidin-1-yl)oxyl.
14. (a) Brill, W., Terephthalic Acid by Single-Stage
Oxidation. Ind. Eng. Chem. 1960, 52, 837-840; (b) Zuo, X.;
Niu, F.; Snavely, K.; Subramaniam, B.; Busch, D. H., Liquid
Phase Oxidation of p-Xylene to Terephthalic Acid at
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Wang, D.; Weinstein, A. B.; White, P. B.; Stahl, S. S.,
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