Desulfonylcyanamidation of α,β-Unsaturated Sulfones with N-tosyl N-Aryl Cyanamides (NCTS): Access to N-Cyanoenaminones

Abstract

Enaminones are versatile building blocks with widespread applications in the synthesis of biologically active molecules, natural products, and synthetic pharmaceutical agents. Herein, we describe a desulfonylcyanamidation between α,β-unsaturated sulfones and cyanamide anions derived in situ from NCTS using CsF as a base. This method provides a facile access to highly desirable chemical products such as N-cyanoenaminones and N-cyanoenaminesters, featuring broad substrate scope, high functional group tolerance, high to excellent yields, and transition-metal-free. Additionally, gram-scale experiments and Lu’s [3 + 2] cycloaddition transformations demonstrated the potential synthetic utility of the transformations.