Copper‐catalyzed one‐pot synthesis of propargylamines via CH activation in PEG

Abstract

An efficient and convenient three-component A 3 coupling reaction of aldehyde, amine and alkyne via C-H activation with CuI alone as the catalyst in PEG is developed, providing a wide range of propargylamines with yields ranging from moderate to excellent. Additionally, the catalyst system was recovered and reused several times without evident loss in activity. Copyright

Copper‐Catalyzed Double Decarboxylative Coupling Reactions of Alkynyl Carboxylic Acid and Glyoxylic Acid: Synthesis of Propargyl Amines and Imidazopyridines

“…4‐[3‐(4‐Methoxyphenyl)‐1‐phenylprop‐2‐yn‐1‐yl]morpholine (4 g) : 3‐(4‐Methoxyphenyl)propiolic acid (176 mg, 1.0 mmol), phenylglyoxylic acid (150 mg, 1.0 mmol), and morpholine (174 mg, 2.0 mmol) afforded product 4 g (233.6 mg, 0.76 mmol, 76 % yield) as a yellow oil. 1 H NMR (300 MHz, CDCl 3 ): δ =7.63 (d, J =6.8 Hz, 2 H), 7.44 (d, J =8.9 Hz, 2 H), 7.40–7.29 (m, 3 H), 6.86 (d, J =8.9 Hz, 2 H), 4.76 (s, 1 H), 3.82 (s, 3 H), 3.73 (m, 4 H), 2.62 ppm (t, J =4.1 Hz, 4 H); 13 C{ 1 H} NMR (75 MHz, CDCl 3 ): δ =159.5, 138.0, 133.2, 128.6, 128.2, 127.7, 115.1, 113.9, 88.3, 83.5, 67.2, 62.1, 55.3, 49.9 ppm; MS (EI): m / z : 307 [ M ] + .…”

Solvent‐free synthesis of propargylamines catalyzed by an efficient recyclable ZnO‐supported CuO/Al2O3 nanocatalyst

“…According to previous reports, various metal‐based catalysts, including Ag, Fe, Li, Ni, Pd, In and Au, have been reported for the synthesis of propargylamines . In this view, copper and zinc catalysts are the most important for the synthesis of propargylamine derivatives, and good results have been achieved in the presence of these catalysts …”

CuII@PAA/PVC mesoporous fibers: A hybrid wedding as a high‐performance versatile heterogeneous catalyst for A3, KA2, and decarboxylative A3 reactions

“…Several reviews have thoroughly highlighted the progress of A 3 couplings for the synthesis of propargylamines and their derivatives via different strategies . An efficient homogeneous transition metal‐based catalytic system for A 3 couplings has been documented in the past decade and the range of reported catalysts included Cu(I), Ag(I), Au(I) or Au (III), Fe (III), Zn, and Cu I /Cu II , Ru III /CuI bimetallic system. However, most of these protocols suffer from one or more drawbacks, such as the need of high temperature, long reaction times, inert atmosphere, some toxic solvents or costly media like ionic liquids, and and use of homogeneous precious metal catalysts.…”