Highly Efficient Copper-Catalyzed Dehydrogenative Cross-Coupling of Azoles with α-Amino Carbonyl Compounds

Abstract

A novel and highly efficient dehydrogenative cross-coupling­ reaction between α-amino carbonyl compounds and azoles by copper catalysis using di-tert-butyl peroxide (DTBP) as an oxidant is described­. A diverse range of azoles undergo the dehydrogenative imidoylation smoothly with various α-amino carbonyl compounds for the exclusive formation of the corresponding N-imidoyl azoles in high yields under air. The synthetic method has the advantages of good functional-group tolerance, wide substrate scope, excellent yields, and simple operation­, thus providing a convenient and practical protocol for the synthesis of functionalized azoles.

The [3 + 2] Cycloaddition Reaction of N-Substituted Pyrrole-2-carboxaldehydes with Arylalkenes under Copper Catalysis: Access to Dihydropyrrolizine Skeletons

“…Based on the aforementioned experimental results and those reported in literature, we proposed a plausible mechanism of this [3 + 2] cycloaddition reaction as shown in Scheme . First, tert -butoxyl radicals and CuII­(O t Bu) species are generated by heating DTBP in the presence of active CuI species. − Subsequently, the tert -butoxyl radical reacts with substrate 1a via intermolecular hydrogen abstraction, leading to the formation of alkyl radical A .…”