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Updated: Feb 18, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Copper-catalyzed cyanothiolation to incorporate a sulfur-substituted quaternary carbon center
Yubing Huang1, Xianwei Li1, Xu Wang1
1Key Laboratory of Functional Molecular Engineering of Guangdong Province , School of Chemistry and Chemical Engineering , South China University of Technology , Guangzhou 510640 , China . Email: cewuwq@scut.edu.cn ;
Abstract:
Sulfur-containing nitriles have important research value in the life sciences due to their diverse biological activities resulting from the sulfur and cyano functional groups. Herein, a copper-catalyzed cyanothiolation of N-tosylhydrazones with thiocyanates to generate α-arylthioalkanenitriles bearing sulfur-substituted quaternary carbon center atoms has been described. This novel protocol involves the procedure of copper carbene species promoting S-CN bond cleavage and C-CN/C-S bond reconstruction to introduce both sulfur and cyano groups onto a single carbon center. This cyanothiolation reaction will greatly enhance the synthetic utility of carbenoid species as new entries for the construction of diverse heteroatom-containing nitriles via cyanofunctionalization of metal-carbene species.
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