Organic Letters
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Scheme 4. Proposed Mechanism
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̃
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tert-butoxide. Intermediate II results from the corresponding β-
sulfinyl ester or silane, which undergoes β-elimination upon
treatment with base or fluoride. Both I and II assemble at
copper by addition and ligand exchange.13−16 Reductive
elimination leads to the observed product 3 and a copper
species of lower oxidation state. Reoxidation of the latter
regenerates the initial copper complex thereby closing the
catalytic cycle.
In summary, we developed a copper-catalyzed sulfoxidation
of benzylic sp3 C−H bonds. The reaction enables the synthesis
of a wide range of functionalized benzyl sulfoxides using
inexpensive, readily available methylarenes.
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ASSOCIATED CONTENT
* Supporting Information
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S
́
D. S.; Ni, Y.; Fernandez-Fueyo, E.; Lee, M.; Hollmann, F.; Park, C. B.
ACS Catal. 2017, 7, 1563.
The Supporting Information is available free of charge on the
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C.; Haselton, N.; Holl, M. G.; Urheim, E.; Lectka, T. Angew. Chem.,
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General experimental procedure and characterization
AUTHOR INFORMATION
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Corresponding Author
ORCID
Notes
(6) Chen, C.; Xu, X. H.; Yang, B.; Qing, F. L. Org. Lett. 2014, 16,
3372.
The authors declare no competing financial interest.
(7) (a) Mellah, M.; Voituriez, A.; Schulz, E. Chem. Rev. 2007, 107,
5133. (b) Mariz, R.; Luan, X.; Gatti, M.; Linden, A.; Dorta, R. J. Am.
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M.; Rao, M. Angew. Chem., Int. Ed. 2015, 54, 5026. (e) Sipos, G.;
Drinkel, E. E.; Dorta, R. Chem. Soc. Rev. 2015, 44, 3834. (f) Otocka, S.;
Kwiatkowska, M.; Madalinska, L.; Kielbasinski, P. Chem. Rev. 2017,
117, 4147.
(8) (a) Block, E. Garlic and Other Alliums; Royal Society of
Chemistry: Cambridge, 2009. (b) Nohara, T.; Fujiwara, Y.; El-Aasr,
M.; Ikeda, T.; Ono, M.; Nakano, D.; Kinjo, J. Chem. Pharm. Bull. 2017,
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ACKNOWLEDGMENTS
H.Y. thanks the China Scholarship Council for a predoctoral
stipend.
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