Visible-Light Photocatalytic Barbier-Type Reaction of Aziridines and Azetidines with Nonactivated Aldehydes

Abstract

Barbier-type reactions represent a classic reaction type for carbon-carbon bond formation. However, the commonly used stoichiometric metals still hamper their wide application. Considering easy availability and diversification of cyclic amines, herein, we report a visible-light photocatalytic Barbier-type reaction of aziridines and azetidines with unactivated aldehydes. A series of important γ- and δ-amino alcohols are synthesized in the presence of amines as electron donors. What’s more, this transition metal-free protocol displays mild reaction conditions, good functional group tolerance and broad substrate scope. Mechanistic investigations indicate that carbon radicals and carbanions might be generated as the key intermediates.

Cluster Preface: Special Issue Honoring Masahiro Murakami’s Contributions to Science

“…4 An elegant photoinduced Barbier-type reaction of aziridines and azetidines with simple aldehydes is described by Yu and Gui, providing an interesting entry point to 1,n-amino alcohols. 5 Furthermore, Harran describes a powerful synthetic endeavor that leverages the synthetic utility of in situ generated prototropic isomers of 2-acetyl-3-methylpyrrole. 6 Meanwhile, Ohta and Hayashi describe an expeditious route to fused  5 -phosphinines, including detailed explorations into their interesting properties as fluorophores.…”