N,N-dimethyl-beta-alanine as an inexpensive and efficient ligand for palladium-catalyzed Heck reaction.
N,N-Dimethyl-beta-alanine was found to be a more powerful phosphine-free ligand than the previously reported ligand, N,N-dimethylglycine, in the Pd-catalyzed Heck reaction for a variety of aryl bromides, aryl iodides, and activated aryl chlorides with a practical turnover number of 10(3). Both kinetic and theoretical studies suggested that N,N-dimethyl-beta-alanine led to faster oxidative addition of an aryl halide to Pd than N,N-dimethylglycine. [reaction: see text]
Cui
Xin
X
Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.
Li
Zhe
Z
Tao
Chuan-Zhou
CZ
Xu
Yu
Y
Li
Juan
J
Liu
Lei
L
Guo
Qing-Xiang
QX
D002384:Catalysis; D008024:Ligands; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D015091:beta-Alanine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000191:economics
D008024:Ligands; D015091:beta-Alanine; C012924:2,2-dimethyl-beta-alanine; D010165:Palladium