首页|Palladium Complexes with N,O-Bidentate Ligands Based on N-Oxide Units from Cyclic Secondary Amines:Synthesis and Catalytic Application in Mizoroki-Heck Reaction

Palladium Complexes with N,O-Bidentate Ligands Based on N-Oxide Units from Cyclic Secondary Amines:Synthesis and Catalytic Application in Mizoroki-Heck Reaction

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Palladium-catalyzed Mizoroki-Heck reaction is a powerful and efficient method for construction of Csp2-Csp2 bonds.Herein,four pal-ladium complexes(Ⅰ-Ⅳ)with N,O-bidentate ligands(L1—L4)based on N-oxide units from cyclic secondary amines were easily syn-thesized and successfully applied in Mizoroki-Heck reaction of aryl bromides with electron-deficient olefins.X-ray diffraction anal-yses indicated the palladium(Ⅱ)atom of Ⅱ took the distorted square planar geometry and was four-coordinated by nitrogen and ox-ygen atoms from two ligands(L2).Two free chloride ions were presented as counter anions in complex Ⅱ.But the palladium(Ⅱ)center of Ⅳ was coordinated by nitrogen and oxygen atoms from one ligand(L4)as well as two chlorine atoms,which exhibited the nearly square-planar geometry.The study on catalytic properties of palladium complexes revealed that complex Ⅱ exhibited high activity superior to the other complexes.The coupling reactions of a series of aryl bromides and olefin derivatives proceeded in the presence of 2-5 mol％palladium complex Ⅱ,giving the desired products in good to excellent yields.The advantages of this method such as good compatibility of functional groups,high yields,and short reaction times made it more attractive for constructing Csp2-Csp2 bonds in the synthesis of functional molecules and materials.

Palladium complexesN,O-Bidentate ligandsN-Oxide unitsMizoroki-Heck reactionAryl bromideElectron-deficient olefinsC—C couplingHomogeneous catalysisSubstituent effects

Xuefeng Jia、Yanyan Wen、Changhui He、Xianqiang Huang

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Key Laboratory of Magnetic Molecules and Magnetic Information Materials of Ministry of Education,School of Chemistry and Materials Science,Shanxi Normal University,Taiyuan,Shanxi 030032,China

Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology,School of Chemistry & Chemical Engineering,Liaocheng University,Liaocheng,Shandong 252059,China

山西省自然科学基金Innovative Program of Graduate Education in Shanxi Province

201901D1112762023KY464

2024

10.1002/cjoc.202300375

中国化学(英文版)
中国化学会 上海有机化学研究所

中国化学(英文版)

CSTPCD
影响因子：0.848
ISSN：1001-604X
年,卷(期)：2024.42(3)
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