Copper-catalyzed cyanothiolation to incorporate a sulfur-substituted quaternary carbon center. Issue 10 (30th August 2017)

• Record Type: Journal Article
• Authors: Huang, Yubing; Li, Xianwei; Wang, Xu; Yu, Yue; Zheng, Jia; Wu, Wanqing; Jiang, Huanfeng
• Is Part Of: Chemical science. Volume 8:Issue 10(2017)
• Page Start: 7047
• Page End: 7051
• Publication Date: 2017-08-30
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7sc02867a
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A copper-catalyzed cyanothiolation of N -tosylhydrazones with thiocyanates to generate α-arylthioalkanenitriles bearing sulfur-substituted quaternary carbon center atoms has been achieved. 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.