Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 6, Pages 2662-2668Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201406171
Keywords
chemoselectivity; cyanation; hypervalent iodine; thiocyanates; synthetic methods
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Funding
- EPFL
- F. Hoffmann-La Roche, Ltd.
- Marie Curie International Incoming Fellowship [331631]
- European Research Council [334840]
- European Research Council (ERC) [334840] Funding Source: European Research Council (ERC)
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A new method for the cyanation of thiols and disulfides using cyanobenziodoxol(on)e hypervalent iodine reagents is described. Both aliphatic and aromatic thiocyanates can be accessed in good yields in a few minutes at room temperature starting from a broad range of thiols with high chemioselectivity. The complete conversion of disulfides to thiocyanates was also possible. Preliminary computational studies indicated a low energy concerted transition state for the cyanation of the thiolate anion or radical. The developed thiocyanate synthesis has broad potential for various applications in synthetic chemistry, chemical biology and materials science.
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