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Scheme 8. Sterically Controlled Arylation of 5km
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In summary, we have developed regioselective C−H
sulfanylation of aryl sulfoxides with aryl sulfides via Pummerer-
type activation. The initially formed sulfonium salts were
demethylated to yield disulfanylarenes or used as electrophiles
in cross-coupling to afford para-arylated aryl sulfides.
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ASSOCIATED CONTENT
* Supporting Information
■
S
(9) For selected recent examples: (a) Akai, S.; Morita, N.; Iio, K.;
Nakamura, Y.; Kita, Y. Org. Lett. 2000, 2, 2279. (b) Akai, S.; Kawashita,
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TheSupportingInformationisavailablefreeofchargeontheACS
Detailed experimental procedures, full spectroscopic data
for all new compounds (PDF); Crystallographic data
̀
5882. (e) Huang, X.; Patil, M.; Fares, C.; Thiel, W.; Maulide, N. J. Am.
Chem. Soc. 2013, 135, 7312. (f) Eberhart, A. J.; Cicoira, C.; Procter, D. J.
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Int. Ed. 2013, 52, 4008. (h) Eberhart, A. J.; Shrives, H. J.; Alvarez, E.;
Carrer, A.; Zhang, Y.; Procter, D. J. Chem. - Eur. J. 2015, 21, 7428.
AUTHOR INFORMATION
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̈
Corresponding Author
ORCID
(i) Fernan
́
dez-Salas, J. A.; Eberhart, A. J.; Procter, D. J. J. Am. Chem. Soc.
2016, 138, 790. (j) Eberhart, A. J.; Shrives, H.; Zhang, Y.; Carrer, A.;
̈
Parry, A. V. S.; Tate, D. J.; Turner, M. L.; Procter, D. J. Chem. Sci. 2016, 7,
1281. (k) Yanagi, T.; Otsuka, S.; Kasuga, Y.; Fujimoto, K.; Murakami, K.;
Nogi, K.; Yorimitsu, H.; Osuka, A. J. Am. Chem. Soc. 2016, 138, 14582.
Notes
́
(l) Shrives, H. J.; Fernandez-Salas, J.; Hedtke, C.; Pulis, A. P.; Procter, D.
J. Nat. Commun. 2017, 8, 14801. (m)Shang, L.;Chang, Y.; Luo, F.;He, J.-
N.;Huang, X.;Zhang, L.;Kong,L.;Li, K.;Peng, B. J. Am. Chem. Soc.2017,
139, 4211.
The authors declare no competing financial interest.
(10) Similar TfOH-mediated C−S bond formations were reported.
However, the mechanismsofthesereactions areunclear, andthescopeas
well as synthetic utility of the reactions were not fully investigated.
(a) Yamamoto, K.; Shouji, E.; Nishide, H.; Tsuchida, E. J. Am. Chem. Soc.
1993, 115, 5819. (b) Reddy, P. G.; Pal, S. P.; Kumar, P.; Pradeep, C. P.;
Ghosh, S.; Sharma, S. K.; Gonsalves, K. E. ACS Appl. Mater. Interfaces
2017, 9, 17.
(11) The structure of 3ka was unambiguously determined by single-
crystal X-ray diffraction as well as 1H and 13C NMR analysis.
(12) (a) Srogl, J.; Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1997,
119, 12376. (b) Zhang, S.; Marshall, D.; Liebeskind, L. S. J. Org. Chem.
1999, 64, 2796.
ACKNOWLEDGMENTS
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This work was supported by JSPS KAKENHI Grant Numbers
JP25107002, JP15K21722, andJP16H01149, aswell asJSTACT-
C Grant Number JPMJCR12ZE, Japan.
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