Post-synthetic Modification of UMCM-1-NH2 as a Catalyst to Prepare β-Amino Alcohols†

doi:10.7503/cjcu20160551

Abstract

Abstract:

By the method of post-synthetic modification of MOFs, salicylaldehyde was anchored to UMCM-1-NH₂ to give a Schiff base functionalized porous compound UMCM-1-NH-Sal. The copper ion can coordinate with N atoms and O atoms inside the channels of the compound to give another compound UMCM-1-NH-Sal-Cu. The compound could catalyze the ring-opening reaction of epoxides with amines to yield β-amino alcohols, and showed good catalytic performance in such reactions.

Key words: Metal-organic framework, Post-synthetic modification, Epoxide ring-opening reaction, β-Amino alcohol

CLC Number:

O643.3

TrendMD:

LIU Hong, WANG Zhengren, CHEN Hengze, ZHANG Ruichang, CHEN Chao, ZHANG Ning. Post-synthetic Modification of UMCM-1-NH₂ as a Catalyst to Prepare β-Amino Alcohols^†[J]. Chem. J. Chinese Universities, 2016, 37(11): 2012.

Figures/Tables 9

Scheme 1 Synthetic route for UMCM-1-NH-Sal-Cu

Scheme 2 Ring opening reaction of epoxides with amines

Fig.1 1H NMR spectra of UMCM-1-NH2(a) and UMCM-1-Sal(b) digested in DCl/D2O/DMSO-d6

Fig.2 Nitrogen adsorption-desorption isotherms of UMCM-1-NH2(a), UMCM-1-NH-Sal(b) and UMCM-1-NH-Sal-Cu(c)

Fig.3 TG curves of UMCM-1-NH2(a), UMCM-1-NH-Sal(b) and UMCM-1-NH-Sal-Cu(c)

Fig.4 PXRD patterns of simulated UMCM-1-NH2(a), UMCM-1-NH2 in CHCl3(b), UMCM-1-NH-Sal-Cu in CHCl3(c) and UMCM-1-NH-Sal-Cu after catalytic reaction(d)

Table 1 Ring-opening reaction of epichlorohydrin with anilinea

Catalyst	Aniline conversion(%)	Product selectivity(%)
Catalyst	Aniline conversion(%)	A	B
	3	0	0
Cu(acac)₂	14	0	0
UMCM-NH₂	18	99	Trace
UMCM-NH-Sal-Cu	53	99	Trace
NH₂SO₃H^b	89	85	15

Table 2 Ring opening reaction of different epoxides with amines using UMCM-NH-Sal-Cu as catalyst*

Amine conversion(%)	Product selectivity(%) A∶B	Amine conversion(%)	Product selectivity(%) A∶B
48	92∶8	45	95∶5
53	99∶1	50	96∶4
46	94∶6	52	93∶7
56	90∶10	46	89∶11

Scheme 3 Proposed mechanism of the catalytic reaction

References 21

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Post-synthetic Modification of UMCM-1-NH₂ as a Catalyst to Prepare β-Amino Alcohols^†

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