Issue 22, 2023

Synthesis of functionalized sulfilimines via iron-catalyzed sulfur alkylation of sulfenamides with diazo compounds

Abstract

An efficient iron-catalyzed sulfur alkylation of sulfenamides with 2,2,2-trifluorodiazoethane is developed. The reaction proceeds smoothly at room temperature in an open flask, enabling the rapid synthesis of trifluoromethylated sulfilimines in moderate to good yields with broad functional group tolerance. In addition, this operationally simple protocol could also be applied to access cyano- and phosphonyl-functionalized sulfilimines using diazoacetonitrile or diazomethylphosphonate.

Graphical abstract: Synthesis of functionalized sulfilimines via iron-catalyzed sulfur alkylation of sulfenamides with diazo compounds

Supplementary files

Article information

Article type
Communication
Submitted
19 9 2023
Accepted
23 10 2023
First published
23 10 2023

Green Chem., 2023,25, 9092-9096

Synthesis of functionalized sulfilimines via iron-catalyzed sulfur alkylation of sulfenamides with diazo compounds

X. Wu, M. Chen, F. He and J. Wu, Green Chem., 2023, 25, 9092 DOI: 10.1039/D3GC03528J

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