Oxidative Cyclization of N‐Aryl Heteroaryl Methanamines with Arylalkenes

Abstract

We describe a protocol to access quinoline-oxadiazole heterobiaryls. The oxidative (4 + 2)-cyclization/aromatization tandem reaction of N-aryl heteroaryl methanamines with alkenes or alkynes was realized by copper catalysis under aerobic condition.

Visible-Light-Driven Coupling of 1,3,4-Oxadiazoles and Hydroxamic Acid Derivatives

“…1 H NMR spectra were recorded at 400 or 600 MHz (Varian), and 13 C { 1 H} NMR spectra were recorded at 100 or 150 MHz (Varian). 19 F { 1 H} NMR spectra were recorded at 376 MHz. Chemical shifts are reported in ppm downfield from CDCl 3 (δ = 7.26 ppm) for 1 H NMR, and chemical shifts for 13 C NMR spectra are reported in ppm relative to the central CDCl 3 (δ = 77.0 ppm).…”

“…Hence, developing mild and efficient strategies toward the modification of 5-aryl-1,3,4-oxadiazole-2-methylamines is of great importance. Huo’s group described a protocol to access quinoline-oxadiazole heterobiaryls, which require the use of metal catalysts and heat source. While, over the past few decades, visible-light-promoted radical–radical cross-coupling reactions has emerged as economical and environmentally benign tools to construct various scaffolds under mild conditions. − In this context, Xu’s group, Wang’s group, and Huo’s group independently applied photoredox catalysis to synthesize α-C­(sp 3 )-H functionalized 5-aryl-1,3,4-oxadiazole-2-methylamines (Scheme B).…”