General and practical formation of thiocyanates from thiols.
- Frei R Present address: Bern University of Applied Sciences, Solothurnstrasse 102, 2504 Biel (Switzerland).
- Courant T
- Wodrich MD
- Waser J
- 2014-12-19
Published in:
- Chemistry (Weinheim an der Bergstrasse, Germany). - 2015
chemoselectivity
cyanation
hypervalent iodine
synthetic methods
thiocyanates
Iodine
Isomerism
Molecular Conformation
Sulfhydryl Compounds
Thermodynamics
Thiocyanates
English
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.
- Language
-
- English
- Open access status
- green
- Identifiers
-
- DOI 10.1002/chem.201406171
- PMID 25521497
- Persistent URL
- https://folia.unifr.ch/global/documents/279230
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