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Communication
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methodologies. We anticipate that this method will be useful
for a variety of applications for the development of drugs and
agrochemicals.
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
■
S
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Crystallographic data of 14 (CIF) and 16A (CIF)
Experimental procedures and characterization data
AUTHOR INFORMATION
Corresponding Author
■
(12) Chen, M. S.; White, M. C. A Predictably Selective Aliphatic C−
H Oxidation Reaction for Complex Molecule Synthesis. Science 2007,
318, 783−787.
ORCID
̈
(13) (a) Chen, M. S.; White, M. C. Combined Effects on Selectivity
in Fe-Catalyzed Methylene Oxidation. Science 2010, 327, 566−571.
(b) Gormisky, P. E.; White, M. C. Catalyst-Controlled Aliphatic C−H
Oxidations with a Predictive Model for Site-Selectivity. J. Am. Chem.
Soc. 2013, 135, 14052−14055. (c) Howell, J. M.; Feng, K.; Clark, J.
R.; Trzepkowski, L. J.; White, M. C. Remote Oxidation of Aliphatic
C−H Bonds in Nitrogen-Containing Molecules. J. Am. Chem. Soc.
2015, 137, 14590−14593. (d) Zhao, J.; Nanjo, T.; de Lucca, E. C.;
White, M. C. Chemoselective Methylene Oxidation in Aromatic
Molecules. Nat. Chem. 2019, 11, 213−221.
Author Contributions
‡These authors contributed equally.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
We thank F. Berger, M. Heinrich, M. Plutschack, and J.
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Rickmeier (all MPI fu
̈
r Kohlenforschung) for helpful
̈
(14) Burg, F.; Gicquel, M.; Breitenlechner, S.; Pothig, A.; Bach, T.
discussions, and we acknowledge M. Leutzsch for help with
NMR analysis. We are grateful for the help of all analytical
Site- and Enantioselective C−H Oxygenation Catalyzed by a Chiral
Manganese Porphyrin Complex with a Remote Binding Site. Angew.
Chem., Int. Ed. 2018, 57, 2953−2957.
departments of the MPI fu
the MPI fur Kohlenforschung for funding. J.B. acknowledges
̈
r Kohlenforschung, and we thank
̈
(15) (a) Moriyama, K.; Takemura, M.; Togo, H. Direct and
Selective Benzylic Oxidation of Alkylarenes via C−H Abstraction
Using Alkali Metal Bromides. Org. Lett. 2012, 14, 2414−2417.
(b) Kim, Y. H.; Kim, K. S.; Lee, H. K. Oxidation of Benzylic
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with IBX. J. Am. Chem. Soc. 2001, 123, 3183−3185.
́
the Fond der Chemischen Industrie for a Kekule Fellowship.
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