Organic Letters
Letter
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β-diaryl substituted vinyl sulfone 6b in 87% yield. Finally,
dehalogenation mediated by zinc and acetic acid afforded (Z)-
vinyl sulfone 6c in 53% yield. These results illustrate the
powerful utility of the developed process not only as a new
synthetic tool to furnish the β-chlorovinyl sulfone moiety but
also as a useful platform for the efficient construction of
synthetically challenging structures by simple manipulation of
the installed groups.
In summary, we have described a novel method for the
regio- and stereoselective chlorosulfonylation of alkynes by
visible-light-induced photoredox catalysis. A wide range of
alkynes, as well as sulfonyl chlorides, are competent
participants in the free-radical mediated reaction to afford
structurally diverse vinyl sulfones. The present protocol allows
for the generation of sulfonyl radical intermediates from easily
available organosulfonyl chlorides under mild conditions at
room temperature, thus representing an operationally con-
venient alternative to the reported methodologies. Finally, we
expect our findings to be of broad utility in the preparation of
sulfone-derived organic molecules.
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ASSOCIATED CONTENT
* Supporting Information
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Arend, A. B.; Tochowicz, A.; Gotz, M. G. J. J. Enzyme Inhib. Med.
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The Supporting Information is available free of charge on the
Experimental procedures, spectroscopic data for all new
compounds and the X-ray crystallographic data of
compound 5g (CCDC 1843966) (PDF)
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Accession Codes
CCDC 1843966 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
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AUTHOR INFORMATION
Corresponding Authors
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ORCID
Notes
The authors declare no competing financial interest.
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Lett. 2017, 19, 2580. (e) Meyer, A. U.; Jager, S.; Hari, D. P.; Konig, B.
Adv. Synth. Catal. 2015, 357, 2050. (f) Katrun, P.;
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Jung, Y.-S.; Han, S. B. Org. Lett. 2017, 19, 1962. (d) An, W.; Ha, N.;
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ACKNOWLEDGMENTS
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Generous support from Korea Research Institute of Chemical
Technology (Grant Nos. KK1803-C00 and KK1706-G08) is
gratefully acknowledged.
REFERENCES
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