Aqueous Suzuki-Miyaura Coupling with Ultralow Palladium Loading and Simple Product Separation
Wei Yang, Wen-Di Xu, Jin-Jiao Ning, Zhi-Gang Ren*, David James Young*
*Soochow University, Suzhou 215123, P. R. of China; Charles Darwin University, Northern Territory 0909, Australia,
Email: renzhigang
suda.edu.cn; david.youngcdu.edu.au
W. Yang, W.-D. Xu, J.-J. Ning, Z.-G. Ren, D. J. Young, Synlett, 2020, 31, 1303-1307.
DOI: 10.1055/s-0040-1707515
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Abstract
A complex of diphosphine ligand N,N-bis(diphenylphosphanylmethyl)-aniline (bdppma) and PdCl2 catalyzes the Suzuki-Miyaura coupling at an ultralow catalyst loading. The use of an aqueous solvent system permitted simple product filtration without the need for chromatography. However, the catalytic system has a slightly narrower substrate scope than some similar Pd catalysts reported previously.
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Details
The document discusses the development of a highly efficient Suzuki–Miyaura catalyst, [(bdppma)PdCl2], which operates at an ultralow catalyst loading (0.001 mol%) in a 20:1 H2O–EtOH solvent system. This catalyst, formed from PdCl2 and the diphosphine ligand N,N-bis(diphenylphosphanylmethyl)-aniline (bdppma), allows for simple product separation by direct filtration, eliminating the need for chromatography. The catalyst demonstrates superior reactivity compared to other bidentate diphosphine ligands but has a slightly narrower substrate scope. The reaction conditions were optimized using 4-bromoacetophenone and phenylboronic acid, achieving a 99% yield with K2CO3 as the base. The catalyst's efficiency was confirmed through various tests, showing high yields even at low catalyst loadings and short reaction times. The study highlights the environmental benefits of using aqueous ethanol and the simplicity of product isolation, making this method advantageous for both laboratory and industrial applications. The research was supported by the National Natural Science Foundation of China and other academic programs.
Key Words
ID: J72-Y2020
