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Iron(III)-Mediated Oxy-Sulfonylation of Enamides with Sodium and Lithium Sulfinates

preprint
submitted on 28.11.2019, 09:34 and posted on 06.12.2019, 08:30 by Philipp Kramer, Miro Halaczkiewicz, Yu Sun, Harald Kelm, Georg Manolikakes

An iron-mediated vicinal difunctionalization of enamides and enecarbamates with sulfinic acid salts and alcohols is described. This reaction proceeds under mild conditions and furnishes the oxy-sulfonylated products in moderate to excellent yields. Moreover, the direct incorporation of sulfur dioxide into the sulfonylated products via organolithium chemistry has been achieved. The formed N-O-acetals are competent acylimine precursors. Their utilization as building block for the synthesis of biologically relevant β-amidosulfones is described as well.

Funding

Deutsche Forschungsgemeinschaft (DFG)

NanoKat

Polytechnische Gesellschaft Frankfurt

History

Email Address of Submitting Author

manolikakes@chemie.uni-kl.de

Institution

TU Kaiserslautern

Country

Germany

ORCID For Submitting Author

0000-0002-4013-5757

Declaration of Conflict of Interest

no conflict of interest

Version Notes

Version 1.0

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in The Journal of Organic Chemistry

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