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Transition metal polymerization catalyst containing CO bidentate ligand

A transition metal and catalyst technology, applied in the field of ortho-hydroxyaryl-substituted N-heterocyclic carbene metal compounds, can solve the problems of no reported results and the like

Inactive Publication Date: 2007-10-31
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Wang Baiquan et al have reported the synthesis of an o-hydroxyaryl N-heterocyclic carbene precursor and its palladium allyl compound (Ren, H.; Yao, P.; Xu, S.; Song, H.; Wang, B.J.Organomet.Chem.2007, 692, 2092.), but did not report their results in catalytic olefin polymerization

Method used

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  • Transition metal polymerization catalyst containing CO bidentate ligand
  • Transition metal polymerization catalyst containing CO bidentate ligand
  • Transition metal polymerization catalyst containing CO bidentate ligand

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1 Synthesis of Complex C1

[0068]

[0069] In a 100 mL reaction flask, 1.2 mL (1.7 N, 2.0 mmol) of n-BuLi in hexane was added dropwise to a suspension of 0.41 g (1.0 mmol) of ligand L1 in THF (30 mL) at 0°C , stirred at 0°C for 0.5 hours, slowly warmed to room temperature, and then added 0.33 g (0.5 mmol) of NiCl 2 (PPh 3 ) 2 , stirred overnight at room temperature. The solvent was drained, separated by alumina column chromatography, and 1:1 CH 2 Cl 2 / petroleum ether, and the obtained components were drained of solvent to obtain 0.33 g of complex C1, with a yield of 92%.

[0070] Elemental analysis: measured (calculated) 70.35 (70.68); H, 8.57 (8.76); N, 7.46 (7.85);

[0071] 1 H NMR (400MHz, CDCl 3 ): δ7.19(d, 1H, im-H, J=1.69Hz), 7.12(s, 1H, Ar-H), 7.05(s, 1H, Ar-H), 7.02(d, im-CH, J=2.04Hz), 1.66(s, 9H, C(CH) 3 ), 1.54(s, 9H, C(CH) 3 ), 1.37(s, 9H, C(CH) 3 );

Embodiment 2

[0072] Example 2 Synthesis of Complex C2

[0073]

[0074] In a 100 mL reaction flask, 1.2 mL (1.7 N, 2.0 mmol) of n-BuLi in hexane was added dropwise to a suspension of 0.44 g (1.0 mmol) of ligand L2 in THF (30 mL) at 0°C , stirred at 0°C for 0.5 hours, slowly warmed to room temperature, and then added 0.33 g (0.5 mmol) of NiCl 2 (PPh 3 ) 2 , stirred overnight at room temperature. The solvent was drained, separated by alumina column chromatography, and 1:1 CH 2 Cl 2 / petroleum ether rinsing, the obtained components were drained of solvent to obtain 0.37g of complex C2, and the yield was 95%.

[0075] Elemental analysis: measured (calculated) 72.07 (72.15); H, 8.95 (8.69); N, 7.52 (7.32);

[0076] 1 H NMR (300MHz, CDCl 3 ): δ7.22(d, 1H, im-CH, J=1.94Hz), 7.19(d, 1H, Ar-H, J=2.40Hz), 7.04(d, 1H, Ar-H, J=2.40Hz ), 6.93(d, 1H, im-CH, J=1.96Hz), 3.52(m, 1H, N(CH)(CH2)5), 1.55(s, 9H, C(CH) 3 ), 1.34(s, 9H, C(CH) 3 ), 1.75~1.26 (m, 10H, (CH 2 ) 5 );

Embodiment 3

[0077] Example 3 Synthesis of Complex C3

[0078]

[0079] In a 100 mL reaction flask, 1.2 mL (1.7 N, 2.0 mmol) of n-BuLi in hexane was added dropwise to a suspension of 0.47 g (1.0 mmol) of ligand L3 in THF (30 mL) at 0°C , stirred at 0°C for 0.5 hours, slowly warmed to room temperature, and then added 0.33 g (0.5 mmol) of NiCl 2 (PPh 3 ) 2 , stirred overnight at room temperature. The solvent was drained, separated by alumina column chromatography, and 1:1 CH 2 Cl 2 / petroleum ether rinsing, and the obtained components were drained of solvent to obtain 0.41 g of complex C3, with a yield of 97%.

[0080] Elemental analysis: measured (calculated) 74.08 (74.55); H, 8.21 (7.94); N, 6.53 (6.69);

[0081] 1 H NMR (300MHz, CDCl 3 ): δ 7.26(s, 1H, Ar-H), 6.91(s, 1H, im-CH), 6.90(s, 1H, im-CH), 6.72(s, 1H, Ar-H), 6.64(s , 2H, Ar-H), 3.53(s, 3H, Ar-CH 3 ), 2.26(s, 3H, Ar-CH 3 ), 1.80 (s, 3H, Ar-CH 3 ), 1.56(s, 9H, C(CH) 3 ), 1.45(s, 9H, C(CH) 3 );

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Abstract

The invention discloses a transient metal polymerization catalyst with [CO] double teeth ligand and synthesis and appliance, which is characterized by the following: including polyolefin polymerization of N-heterocyclic carbene ligand with ortho-hydroxyl group aryl replacement, method for synthesizing and application research. This activator relates to the third tufts to the eleven tufts transient metal complex with a new type double teeth ligand.

Description

technical field [0001] The invention relates to a N-heterocyclic carbene metal compound substituted by an o-hydroxyaryl group, a synthesis method and a homogeneous (directly used without loading) or heterogeneous (after loading with carriers such as silicon oxide, aluminum oxide, magnesium chloride, etc. Application research on the polymerization of cyclic olefins catalyzed by using ). This type of compound relates to a transition metal compound from the third group to the eleventh group of a novel bidentate ligand. Background technique [0002] N-heterocyclic carbene is a two-electron donor with a strong σ-donating ability and a weak ability to accept feedback π-electrons. These properties provide their metal compounds with properties different from other traditional neutral ligands. It has been reported that N-heterocyclic carbene complexes of some metals have higher reactivity and catalytic activity than their traditional complexes (Scholl, M.; Ding, S.; Lee, C.W.; Grub...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F4/642C08F4/652C08F32/00
Inventor 王佰全任鸿平徐善生
Owner NANKAI UNIV
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