Reusable Cu2O/PPh3/TBAB system for the cross-couplings of aryl halides and heteroaryl halides with terminal alkynes.
An efficient and reusable Cu2O/PPh3/TBAB (n-Bu4NBr) system for the cross-coupling reactions of aryl and heteroaryl halides with terminal alkynes has been developed. Four types of Cu2O, including bulky Cu2O, cubic Cu2O nanoparticles, octahedral Cu2O nanoparticles, and spherical Cu2O nanoparticles, were examined, and the octahedral Cu2O nanoparticles were found to be the most effective catalyst for the reaction. In the presence of the octahedral Cu2O nanoparticles, PPh3, and TBAB, a variety of aryl and heteroaryl halides were reacted with alkynes including alkynols smoothly in moderate to good yields. Noteworthy is that the Cu2O/PPh3/TBAB system can be recovered and reused several times without loss of any activities.
Tang
Bo-Xiao
BX
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, China.
Wang
Feng
F
Li
Jin-Heng
JH
Xie
Ye-Xiang
YX
Zhang
Man-Bo
MB
D000480:Alkynes / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002625:Chemistry, Organic / Q000295:instrumentation / Q000379:methods; D003300:Copper / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D008956:Models, Chemical; D036103:Nanotechnology / Q000295:instrumentation / Q000379:methods; D037742:Nanotubes, Carbon / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry*
D000480:Alkynes; D006219:Halogens; D037742:Nanotubes, Carbon; D010720:Phosphines; D002244:Carbon; D003300:Copper; C044646:phosphine