Unexpected Reactivity of Nitrones: Catalytic Insertion of CS2
Marcos López-Aguilar1, Nicolás Ríos-Lombardía1, Daniel Barrena-Espés1
1Physical and Analytical Chemistry Department, Universidad de Oviedo, Avenida Julián Clavería 8, 33006 Oviedo, Asturias, Spain.
None:
A new reactivity mode for nitrones is reported, consisting of the chloride-catalyzed insertion of CS2 to afford thioamides. This reaction proceeds under metal-free and mild conditions, tolerates a broad family of substrates, and is robust and easily scalable, being successfully applied to the synthesis of the HIV-1 reverse transcriptase inhibitor UC-781. Mechanistic studies, supported by DFT calculations, have revealed the role of chloride anions in the activation of CS2 and its subsequent insertion into nitrones.
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