Electrochemical Isothiocyanation of Primary Amines.

Isothiocyanates are ubiquitous building blocks used across the fields. Nevertheless, their classical syntheses very often rely on the use of toxic and expensive reagents. Herein, we report a new practical, mild, high-yielding, and supporting-electrolyte-free electrochemical method for the preparation of aliphatic and aromatic isothiocyanates from amine and carbon disulfide.

[1]  K. Lam Electrosynthesis: A Practical Way to Access Highly Reactive Intermediates , 2022, Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry.

[2]  M. Leech,et al.  A practical guide to electrosynthesis , 2022, Nature Reviews Chemistry.

[3]  Tao Wang,et al.  Electrochemical Benzylic C(sp3)-H Isothiocyanation. , 2022, Organic letters.

[4]  F. Prinz,et al.  Discovery of BAY-985 a highly selective TBK1/Ikkε inhibitor. , 2019, Journal of medicinal chemistry.

[5]  R. Arora,et al.  Molecular targets in cancer prevention by 4-(methylthio)butyl isothiocyanate - A comprehensive review. , 2019, Life sciences.

[6]  S. Wen,et al.  New Mild and Simple Approach to Isothiocyanates: A Class of Potent Anticancer Agents , 2017, Molecules.

[7]  B. Shaik,et al.  Cobalt mediated by desulfurization toward the synthesis of isothiocyanates , 2016 .

[8]  A. M. Qureshi,et al.  Thiourea Derivatives in Drug Design and Medicinal Chemistry: A Short Review , 2016 .

[9]  Guirong Zhang,et al.  DBU and DBU‐Derived Ionic Liquid Synergistic Catalysts for the Conversion of Carbon Dioxide/Carbon Disulfide to 3‐Aryl‐2‐oxazolidinones/[1,3]Dithiolan‐2‐ylidenephenyl‐ amine , 2016 .

[10]  J. B. Christensen,et al.  A new efficient synthesis of isothiocyanates from amines using di-tert-butyl dicarbonate , 2008 .

[11]  R. N. Brogden,et al.  Cefodizime. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. , 1992, Drugs.

[12]  K. Lam,et al.  Electrochemical deoxygenation of primary alcohols , 2012 .

[13]  Satyavan Sharma THIOPHOSGENE IN ORGANIC SYNTHESIS , 1978 .

[14]  S. J. Cyvin,et al.  The Association of Alkali Metal N,N-Dialkyldithiocarbamates in Solution. , 1971 .