Organic Letters
Letter
were reliant on the presence of a Lewis base catalyst. These
results are significant for two reasons. First, they represent a mild
and efficient route for the addition of diverse sulfur containing
functionalities into arenes. Second, the potential for autocatalysis
can have implications when developing regio- or enantioselective
sulfenylation, an area that has recently received significant
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ASSOCIATED CONTENT
Supporting Information
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S
(13) Yadav, J. S.; Reddy, B. V. S.; Reddy, Y. J. A Rapid Synthesis of 3-
Sulfenyl Indoles Using Selectfluor. Tetrahedron Lett. 2007, 48, 7034−
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(
15) Tudge, M.; Tamiya, M.; Savarin, C.; Humphrey, G. R.
Development of a Novel, Highly Efficient Halide-Catalyzed Sulfenyla-
AUTHOR INFORMATION
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tion of Indoles. Org. Lett. 2006, 8, 565−568.
(16) Gillis, H.; Greene, L.; Thompson, A. Preparation of Sulfenyl
Pyrroles. Synlett 2009, 2009, 112−116.
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ORCID
Sulfenylation of Aromatics Using Highly Active Quinone Mono O,S-
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2, 1077−1080.
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Arylthiation of Substituted Phenols at Room Temperature. Chem.
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The authors declare no competing financial interest.
(
19) Hostier, T.; Ferey, V.; Ricci, G.; Gomez Pardo, D.; Cossy, J.
ACKNOWLEDGMENTS
Synthesis of Aryl Sulfides: Metal-Free C−H Sulfenylation of Electron-
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Rich Arenes. Org. Lett. 2015, 17, 3898−3901.
Primary support for this project came from the National Science
Foundation (Che-1664565). E.A. is thankful for support from
the SDSU LSAMP National Science Foundation (HRD-
(20) Nalbandian, C. J.; Miller, E. M.; Toenjes, S. T.; Gustafson, J. L. A
Conjugate Lewis Base-Bronsted Acid Catalyst for the Sulfenylation of
Nitrogen Containing Heterocycles under Mild Conditions. Chem.
Commun. 2017, 53, 1494−1497.
1302873). We would like to thank Professor Byron Purse
(
SDSU) for insightful discussions, Professor Erica Forsberg and
(21) Luo, J.; Zhu, Z.; Liu, Y.; Zhao, X. Diaryl Selenide Catalyzed Vicinal
Brijinder Soni for help obtaining HRMS, and Dr. Bennett
Addison (SDSU) for technical support regarding NMR.
Trifluoromethylthioamination of Alkenes. Org. Lett. 2015, 17, 3620−
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(22) Zhu, Z.; Luo, J.; Zhao, X. Combination of Lewis Basic Selenium
Catalysis and Redox Selenium Chemistry: Synthesis of Trifluorome-
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