Copper Nanoparticles Catalyzed Three-Component Coupling of Alkyne, Dihalomethane and Amine for the Synthesis of Propargylic Amine

Abstract

A copper nanoparticles-catalyzed three-component coupling reaction of alkyne, dihalomethane, and amine (AHA coupling) was reported for the synthesis of propargylic amine. The catalytic AHA coupling reaction was carried out under mild conditions with dihalomethane as substrate and solvent, and good to excellent yields were also achieved. Furthermore, the nanoparticle catalyst could be recovered and reused effectively, and no obvious reduction on catalytic activity was observed for five recycles.

Recyclable Cu/C3N4 composite catalyzed AHA/A3 coupling reactions for the synthesis of propargylamines

“…To understand the effect of C 3 N 4 support on the catalytic activity, a controlled experiment was carried out, in which Cu NPs was used as catalyst. Obviously, without additional strong base, 15 much worse result was observed (entry 12). This result might indicate that the C 3 N 4 support increased the catalytic activity of copper species successfully under current conditions.…”

“…In our previous work, a Cu NPs-catalyzed AHA reaction was accomplished in CH 2 Cl 2 solution. 15 Although a highly catalytic activity was observed, additional strong base (Cs 2 CO 3 ) was also required in the reaction and only low recyclability of the Cu NPs catalyst was observed. On the other hand, a metal-free AHA reaction was also developed, but only moderate yields were obtained.…”

Atomically precise nanocluster-catalyzed coupling reactions

“…Similar to A 3 coupling, the multicomponent coupling reaction of alkyne, halomethane, and amine (AHA) produces propargylamines. To date, remarkable efforts have been made on this system by applying metal catalysts such as Cu, 157,158 In, 159 Fe, 160 Co, 161 Ni, 139 Ag, 162 and Au. 163,164 A metal-free version of the AHA coupling was also developed but with mediocre yields.…”