Effects of Anchoring Group on the Catalytic Activity of HKUST-1/TEMPO Co-catalysts †

doi:10.7503/cjcu20190683

Abstract

Abstract:

By using isonicotinic acid(Iso-NTA) as a bridging molecule, a pyridyl functionalized 2,2,6,6-tetramethylpiperidinyl-1-oxy(TEMPO) radical(Iso-NTA-TEMPO) was synthesized by the condensation of 4-amino-2,2,6,6-tetramethylpiperidino-1-oxy(4-NH₂-TEMPO) and isonicotinic acid. Compared with TEMPO, Iso-NTA-TEMPO exhibited higher oxidation potential, which facilitates the oxidation reaction of benzyl alcohol, without the use of Cu(Ⅱ). In the case of Iso-NTA-TEMPO/HKUST-1 hybrid catalytic system, the Iso-NTA-TEMPO can be(partially) coordinated to Cu(Ⅱ) sites of HKUST-1 by pyridyl group during catalysis. As consequence, the Iso-NTA-TEMPO/HKUST-1 catalytic system shows much higher catalytic activity than that of TEMPO/HKUST-1 system, toward the oxidation of aromatic alcohols. Moreover, HKUST-1 synthesized by template assisted solvent-induced crystallization consists a significant amount of defects, which facilitates the diffusion of Iso-NTA-TEMPO into the pores of HKUST-1, thus, improving the catalytic activity of Iso-NTA-TEMPO/HKUST-1. The Iso-NTA-TEMPO/HKUST-1 system enables the oxidation of a broad range of primary aromatic alcohols with various substituted groups and heteroatoms, as well as secondary aliphatic alcohols with high efficiency and selectivity.

Key words: HKUST-1, 2,2,6,6-Tetramethylpiperidinyl-1-oxy(TEMPO) radicals, Anchoring group, Co-catalyst, Template

CLC Number:

O643

TrendMD:

XUE Yun,YAN Mi,SHEN Yanming,MAO Huiling,WANG Chen,CHENG Hu,ZHUANG Jinliang. Effects of Anchoring Group on the Catalytic Activity of HKUST-1/TEMPO Co-catalysts ^†[J]. Chem. J. Chinese Universities, 2020, 41(5): 1068.

Figures/Tables 11

References 29

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Entry	Catalyst	Co-catalyst	Activator	Time/h	Conversion^b(%)	Selectivity^b(%)
1	—	Iso-NTA-TEMPO	TBN	1.5	64	>99
2	—	TEMPO	TBN	1.5	18	>99
3	HKUST-1	Iso-NTA-TEMPO	TBN	1.5	>99	>99
4	HKUST-1	TEMPO	TBN	1.5	30	>99
5	HKUST-1	Iso-NTA-TEMPO	—	24	36	>99
6	HKUST-1	TEMPO	—	24	23	>99
7	HKUST-1	—	—	24	<1	—
8	Cu(NO₃)₂·3H₂O	Iso-NTA-TEMPO	TBN	1.5	43	>99
9	Cu(NO₃)₂·3H₂O	TEMPO	TBN	1.5	34	>99

Entry	Catalyst	Co-catalyst	Activator	Time/h	Conversion^b(%)	Selectivity^b(%)
1	—	Iso-NTA-TEMPO	TBN	1.5	64	>99
2	—	TEMPO	TBN	1.5	18	>99
3	HKUST-1	Iso-NTA-TEMPO	TBN	1.5	>99	>99
4	HKUST-1	TEMPO	TBN	1.5	30	>99
5	HKUST-1	Iso-NTA-TEMPO	—	24	36	>99
6	HKUST-1	TEMPO	—	24	23	>99
7	HKUST-1	—	—	24	<1	—
8	Cu(NO₃)₂·3H₂O	Iso-NTA-TEMPO	TBN	1.5	43	>99
9	Cu(NO₃)₂·3H₂O	TEMPO	TBN	1.5	34	>99

Entry	Time/h	Conversion^b(%)	Selectivity^b(%)
1	3	91	>99
2	1.5	>99	>99
3	6	>99	>99
4	3	98	>99
5	1.5	>99	>99
6	6	>99	>99
7	12	>99	>99
8	12	>99	>99
9	12	>99	>99
10	12	>99	>99

Entry	Time/h	Conversion^b(%)	Selectivity^b(%)
1	3	91	>99
2	1.5	>99	>99
3	6	>99	>99
4	3	98	>99
5	1.5	>99	>99
6	6	>99	>99
7	12	>99	>99
8	12	>99	>99
9	12	>99	>99
10	12	>99	>99