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Updated: Apr 19, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
General and practical formation of thiocyanates from thiols
Reto Frei1, Thibaut Courant, Matthew D Wodrich
1Present address: Bern University of Applied Sciences, Solothurnstrasse 102, 2504 Biel (Switzerland).
A novel method enables rapid, room-temperature synthesis of thiocyanates from thiols and disulfides using hypervalent iodine reagents. This efficient cyanation reaction offers broad applications in synthetic chemistry and materials science.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Thiocyanates are valuable synthetic intermediates.
- Efficient methods for thiocyanate synthesis are crucial.
Purpose of the Study:
- To develop a new, efficient method for synthesizing thiocyanates.
- To utilize hypervalent iodine reagents for the cyanation of thiols and disulfides.
Main Methods:
- Cyanation of thiols and disulfides using cyanobenziodoxolone.
- Room temperature reaction conditions.
- High chemoselectivity.
Main Results:
- Access to both aliphatic and aromatic thiocyanates in good yields.
- Rapid reaction times (minutes).
- Complete conversion of disulfides to thiocyanates achieved.
- Computational studies suggest a low-energy concerted transition state.
Conclusions:
- A versatile and efficient method for thiocyanate synthesis has been developed.
- The method is applicable to a broad range of substrates.
- Potential applications in synthetic chemistry, chemical biology, and materials science.
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