N,N-dimethyl-beta-alanine as an inexpensive and efficient ligand for palladium-catalyzed Heck reaction

作者:Cui Xin; Li Zhe; Tao Chuan Zhou; Xu Yu; Li Juan; Liu Lei*; Guo Qing Xiang
来源:Organic Letters, 2006, 8(12): 2467-2470.
DOI:10.1021/ol060585n

摘要

N, N-Dimethyl-ss-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-ss-alanine led to faster oxidative addition of an aryl halide to Pd than N, N-dimethylglycine.