Palladium-Catalyzed Site-Selective sp3 C-H Bond Thiocyanation of 2-Aminofurans.

Abstract

Alkyl thiocyanates are prevalent in natural products, drugs, and biologically active compounds. We report here a novel, mild, and efficient Pd-catalyzed site-selective sp3 C-H bond thiocyanation of 2-aminofurans. Using Na2S2O8 as the oxidant and readily available NaSCN as the thiocyanation reagent, the kinetically favorable 2-amino-4-thiocyanatomethylfurans are selectively synthesized in promising yields with a broad substrate scope. This reaction represents the first example of transition-metal-catalyzed site-selective sp3 C-H bond thiocyanation, thus offering a novel strategy for the step- and atom-economic synthesis of alkyl thiocyanates.