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und Aertzte; Strassburg, 1885.
Conclusion
A novel oxidative method for producing sulfonates from sulfi-
nates using hypervalent iodine reagents has been developed.
This process involves the formation of a reactive sulfonium
species that is subsequently trapped by nucleophiles. As a proof
of concept, we demonstrated that the method is extendable to
other nucleophiles such as electron-rich aromatics or THF.
Ongoing investigations of this process and potential applica-
tions will be disclosed in due course.
6. Tamura, Y.; Yakura, T.; Haruta, J.; Kita, Y. J. Org. Chem. 1987, 52,
7. Farid, U.; Malmedy, F.; Claveau, R.; Albers, L.; Wirth, T.
Angew. Chem., Int. Ed. 2013, 52, 7018–7022.
8. Zhdankin, V. V. Hypervalent Iodine Chemistry: Preparation, Structure,
and Synthetic Applications of Polyvalent Iodine Compounds; John
9. Coffinier, R.; El Assal, M.; Peixoto, P. A.; Bosset, C.; Miqueu, K.;
Sotiropoulos, J.-M.; Pouységu, L.; Quideau, S. Org. Lett. 2016, 18,
Experimental
10.Jacquemot, G.; Maertens, G.; Canesi, S. Chem. – Eur. J. 2015, 21,
General procedure for the formation of
sulfonate 4
11.Coulibali, S.; Godou, T.; Canesi, S. Org. Lett. 2016, 18, 4348–4351.
Iodobenzene diacetate (DIB, 0.24 mmol, 1.2 equiv) was added
at room temperature to a vigorously stirred solution of dichloro-
methane (0.5 mL), alcohol (0.5 mL), sulfinate (0.2 mmol,
1 equiv) and acetic acid (0.01 to 0.05 mL) or TBAC (55.5 mg,
0.2 mmol, 2 equiv) to dissolve the sulfonate salt. The mixture
was then stirred for 15 min and filtered on silica with ethyl
acetate. The residue was purified using silica gel chromatogra-
phy to yield sulfonate product 4.
12.Coulibali, S.; Deruer, E.; Godin, E.; Canesi, S. Org. Lett. 2017, 19,
13.Martínez, C.; Muñiz, K. Angew. Chem., Int. Ed. 2015, 54, 8287–8291.
14.Antien, K.; Viault, G.; Pouységu, L.; Peixoto, P. A.; Quideau, S.
15.Uyanik, M.; Sasakura, N.; Mizuno, M.; Ishihara, K. ACS Catal. 2017, 7,
16.Mizar, P.; Niebuhr, R.; Hutchings, M.; Farooq, U.; Wirth, T.
17.Shimogaki, M.; Fujita, M.; Sugimura, T. Angew. Chem., Int. Ed. 2016,
Supporting Information
Supporting Information File 1
18.Deruer, E.; Coulibali, S.; Boukercha, S.; Canesi, S. J. Org. Chem.
19.Kita, Y.; Morimoto, K.; Ito, M.; Ogawa, C.; Goto, A.; Dohi, T.
20.Dohi, T.; Ito, M.; Yamaoka, N.; Morimoto, K.; Fujioka, H.; Kita, Y.
Angew. Chem., Int. Ed. 2010, 49, 3334–3337.
General procedures, synthesis of the products,
spectroscopic data, and copies of 1H, 13C, NMR spectra.
21.Morimoto, K.; Yamaoka, N.; Ogawa, C.; Nakae, T.; Fujioka, H.;
Dohi, T.; Kita, Y. Org. Lett. 2010, 12, 3804–3807.
Acknowledgements
We are very grateful to the Natural Sciences and Engineering
Research Council of Canada (NSERC), the Canada Foundation
for Innovation (CFI), and the provincial government of Quebec
(FQRNT and CCVC) for their precious financial support in this
research.
22.Dohi, T.; Ito, M.; Itani, I.; Yamaoka, N.; Morimoto, K.; Fujioka, H.;
23.Morimoto, K.; Sakamoto, K.; Onishi, Y.; Miyamoto, T.; Ito, M.; Dohi, T.;
Kita, Y. Chem. – Eur. J. 2013, 19, 8726–8731.
24.Ito, M.; Kubo, H.; Itani, I.; Morimoto, K.; Dohi, T.; Kita, Y.
25.Jean, A.; Cantat, J.; Bérard, D.; Bouchu, D.; Canesi, S. Org. Lett. 2007,
ORCID® iDs
26.Jacquemot, G.; Ménard, M.-A.; L’Homme, C.; Canesi, S. Chem. Sci.
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