Access to 4-substituted isothiazoles through three-component cascade annulation and their application in C–H activation?

Chemical Communications Pub Date: 2020-04-08 DOI: 10.1039/D0CC01100B

Abstract

The use of potassium ethyl xanthate (EtOCS2k) as a sulfur atom donor enabled the transition-metal-free [3 + 1 + 1] cascade annulation of isopropene derivatives with NH4I in DMSO/H2O, affording various 4-substituted isothiazoles in moderate to good yields with good functional group compatibility. Furthermore, Pd and Ag-catalyzed C5–H-selective direct oxidation dimerization of 4-substituted isothiazoles afforded 5,5′-bisisothiazoles. This series of reactions included the formation of new C–S, C–N, N–S, and C–C bonds via cascade addition, annulation, and direct C–H activation under mild conditions.

Graphical abstract: Access to 4-substituted isothiazoles through three-component cascade annulation and their application in C–H activation
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