Photoredox and Cobalt Co-catalyzed Dehydrogenative Ring-opening/Functionalization of Mono-donor Cyclopropanes

Abstract

Catalytic ring-opening/functionalization of unactive cyclopropanes has proven to be a significant but challenging task in organic synthesis. Herein, we disclose the photoredox and cobalt co-catalyzed ring-opening/acceptorless dehydrogenative functionalization of mono-donor cyclopropanes, which provides a promising platform to achieve a sustainable and atom-economic approach to assemble allylic N-acyl-acetal derivatives. The reaction features mild condition, broad substrate scopes and excellent functional group compatibilities. The optimized conditions accommodate various cycloalkylamides and primary, secondary and tertiary alcohols, with applications in late-stage functionalization of pharmaceutically relevant compounds, stimulating the further utility in medicinal chemistry. Selective nucleophilic substitutions and further transformations of desired products with various carbon nucleophiles were succeed in a one-pot fashion, thus offering diverse acyclic or cyclic derivatives.