Reusable copper-catalyzed cross-coupling reactions of aryl halides with organotins in inexpensive ionic liquids.
A combination of Cu2O nanoparticles with P(o-tol)3 shows highly catalytic activity for the Stille cross-coupling reaction. A series of copper catalysts and ligands were evaluated, and Cu2O nanoparticles combined with P(o-tol)3 provided the best results. In the presence of Cu2O nanoparticles and P(o-tol)3, a variety of aryl halides including aryl chlorides underwent the Stille reaction with organotins smoothly in moderate to excellent yields using inexpensive TBAB (n-Bu4NBr) as the medium. It is noteworthy that the Cu2O/P(o-tol)3/TBAB system can be recovered and reused at least three times without any loss of catalytic activity among the reactions of aryl iodides and activated aryl bromides.
Li
Jin-Heng
JH
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, China. jhli@hunnu.edu.cn
Tang
Bo-Xiao
BX
Tao
Li-Ming
LM
Xie
Ye-Xiang
YX
Liang
Yun
Y
Zhang
Man-Bo
MB
D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D052578:Ionic Liquids / Q000737:chemistry*; D053768:Metal Nanoparticles / Q000737:chemistry*; D015394:Molecular Structure; D009947:Organotin Compounds / Q000737:chemistry*
D001555:Benzene Derivatives; D006846:Hydrocarbons, Halogenated; D052578:Ionic Liquids; D009947:Organotin Compounds; D003300:Copper