Highly bulky and stable geometry-constrained iminopyridines: Synthesis, structure and application in Pd-catalyzed Suzuki coupling of aryl chlorides

Yi Lai; Zhijian Zong; Yujie Tang; Weimin Mo; Nan Sun; Baoxiang Hu; Zhenlu Shen; Liqun Jin; Wen-Hua Sun; Xinquan Hu

doi:10.3762/bjoc.13.24

Highly bulky and stable geometry-constrained iminopyridines: Synthesis, structure and application in Pd-catalyzed Suzuki coupling of aryl chlorides

Beilstein J Org Chem. 2017 Feb 3:13:213-221. doi: 10.3762/bjoc.13.24. eCollection 2017.

Authors

Yi Lai¹, Zhijian Zong¹, Yujie Tang¹, Weimin Mo¹, Nan Sun¹, Baoxiang Hu¹, Zhenlu Shen¹, Liqun Jin², Wen-Hua Sun³, Xinquan Hu²

Affiliations

¹ College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032, P.R. China.
² College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032, P.R. China; State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P.R. China.
³ Key laboratory of Engineering Plastics and Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P.R. China.

Abstract

A series of bulky geometry-constrained iminopyridylpalladium chlorides were developed. The steric environment adjacent to the nitrogen atom in the pyridine rings and diimine parts enhanced the thermal stability of the palladium species. Bulkier groups at the imino group stabilized the palladium species and the corresponding palladium chlorides showed high activities in the coupling reaction of aryl chlorides.

Keywords: Suzuki; aryl chloride; geometry-constrained; iminopyridyl; palladium.