Paal-Knorr Reaction Catalyzed by Fe-MIL-101 for Efficient Synthesis of Pyrroles†

doi:10.7503/cjcu20150462

Abstract

Abstract:

A highly porous metal-organic frameworks(Fe-MIL-101) was synthesized as a heterogeneous catalyst for the Paal-Knorr reaction. The free coordination position of Fe(Ⅲ) in Fe-MIL-101 can be used as catalytic active sites for the Paal-Knorr reaction. The large surface area and pore size of Fe-MIL-101 contribute to offer an access for organic substrates to the active sites sufficiently, which ensure a high catalytic performance of Fe-MIL-101 for pyrroles. The catalyst could be reused five times without loss of its catalytic activity. In addition, the catalyst also exhibits high catalytic activity in other amines system with 2,5-hexane-dione for Paal-Knorr condensation reaction.

Key words: Fe-MIL-101 heterogeneous catalyst, Paal-Knorr reaction, Pyrrole derivative

CLC Number:

O643

TrendMD:

YANG Ming, TANG Jia, WANG Jingjing, FAN Shuang, ZHANG Huan, TAO Liushi, TAN Li. Paal-Knorr Reaction Catalyzed by Fe-MIL-101 for Efficient Synthesis of Pyrroles^†[J]. Chem. J. Chinese Universities, 2016, 37(1): 108.

Figures/Tables 8

References 35

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Entry	Catalyst	Time/min	Conversion(%)	Selectivity(%)
1		60	20.4	99.9
2	FeCl₃·6H₂O	50	99.9	99.9
3	Fe(NO₃)₃·9H₂O	50	99.9	99.9
4	Fe₂(SO₄)₃	50	98.8	99.9
5	Fe(C₅H₅)₂	50	13.3	99.9
6	Fe-MIL-101	50	98.9	99.9

Entry	Catalyst	Time/min	Conversion(%)	Selectivity(%)
1		60	20.4	99.9
2	FeCl₃·6H₂O	50	99.9	99.9
3	Fe(NO₃)₃·9H₂O	50	99.9	99.9
4	Fe₂(SO₄)₃	50	98.8	99.9
5	Fe(C₅H₅)₂	50	13.3	99.9
6	Fe-MIL-101	50	98.9	99.9

Entry	Solvent	Time/min	Conversion(%)	Selectivity(%)
1		50	2.4	99.9
2	C₂H₅OH^b	50	9.1	99.9
3	CH₃CN^b	50	12.5	99.9
4	CHC	50	17.7	99.9
5	C₄H₈O^b	50	31.0	99.9
6	C₂H₄C	50	8.7	99.9
7	H₂O^b	50	98.9	99.9
8	C₂H₄C	50	64.1	99.9
9	C₂H₄C	180	99.9	99.9

Entry	Solvent	Time/min	Conversion(%)	Selectivity(%)
1		50	2.4	99.9
2	C₂H₅OH^b	50	9.1	99.9
3	CH₃CN^b	50	12.5	99.9
4	CHC	50	17.7	99.9
5	C₄H₈O^b	50	31.0	99.9
6	C₂H₄C	50	8.7	99.9
7	H₂O^b	50	98.9	99.9
8	C₂H₄C	50	64.1	99.9
9	C₂H₄C	180	99.9	99.9

Entry	Temperature/℃	Time	Conversion(%)	Selectivity(%)
1	60	1 h	1.91	99.9
2	60	24 h	46.8	99.9
3	80	1 h	37.1	99.9
4	80	3 h	89.9	99.9
5	80	6 h	99.5	99.9
6	100	50 min	98.9	99.9
7	100	1 h	99.6	99.9