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Copper-catalyzed cyanothiolation to incorporate a sulfur-substituted quaternary carbon center.

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 ?-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.

SUBMITTER: Huang Y

PROVIDER: S-EPMC5637458 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Copper-catalyzed cyanothiolation to incorporate a sulfur-substituted quaternary carbon center.

Huang Yubing Y Li Xianwei X Wang Xu X Yu Yue Y Zheng Jia J Wu Wanqing W Jiang Huanfeng H

Chemical science 20170815 10

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 <i>N</i>-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 reco ...[more]

PMID: 29147532

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