High Efficency Synthesis of Ferrocenyl Derivatives Catalyzed by Trace Amount Cyclopalladated Complex†

doi:10.7503/cjcu20150624

Abstract

Abstract:

A series of ferrocenyl derivatives with special substituent(1—9) in middle to excellent yields was synthesized by Suzuki-Miyaura cross-coupling reaction using new diferrocenylimine cyclopalladated complex(Fc₂C=NPh)PdClPPh₃(Fc=Ferrocenyl, Ph=Phenyl) as catalyst and Fc-I as reactant. The cross-coupling reaction conditions were optimized and the substrate scope was investigated, and a synthetic route was given for preparing ferrocenyl derivatives and the catalytic reaction mechanism was deduced. The results show that the complex catalyst highlights the features of high catalytic activity, trace catalyst loading, wide substrate scope, excellent reaction efficiency and insensitive to air and moisture for synthesizing ferrocenyl derivatives.

Key words: Cyclopalladated complex, High active palladium catalyst, Cross-coupling, Ferrocenyl derivative, Reaction mechanism

CLC Number:

O643
O621.3

TrendMD:

SUO Quanling, ZHANG Danzhao, KE Chunlong, ZHU Ning, GAO Yuanyuan, XIE Ruijun, HAN Limin. High Efficency Synthesis of Ferrocenyl Derivatives Catalyzed by Trace Amount Cyclopalladated Complex^†[J]. Chem. J. Chinese Universities, 2016, 37(3): 552.

Figures/Tables 4

References 35

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Entry	Catalyst	n_catalyst/μmol	Time/h	Yield^b(%)
1	Blank contrast	0	5	0
2	PdCl₂	0.50	10	trace
3^c	PdCl₂(PPh₃)₂	0.50	12	43.1
4^c	Pd(PPh₃)₄	0.50	9	70.0
5^c	[Fc(CH₃)C═NPh]PdClPPh₃	0.50	5	75.3
6	(Fc₂C═NPh)PdClPPh₃	0.45	5	62.8
7	(Fc₂C═NPh)PdClPPh₃	0.50	5	83.2
8	(Fc₂C═NPh)PdClPPh₃	1.00	5	83.4

Entry	Catalyst	n_catalyst/μmol	Time/h	Yield^b(%)
1	Blank contrast	0	5	0
2	PdCl₂	0.50	10	trace
3^c	PdCl₂(PPh₃)₂	0.50	12	43.1
4^c	Pd(PPh₃)₄	0.50	9	70.0
5^c	[Fc(CH₃)C═NPh]PdClPPh₃	0.50	5	75.3
6	(Fc₂C═NPh)PdClPPh₃	0.45	5	62.8
7	(Fc₂C═NPh)PdClPPh₃	0.50	5	83.2
8	(Fc₂C═NPh)PdClPPh₃	1.00	5	83.4