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Phosphonium salt compound containing precursor of biphosphorus ylide cyclopentadienyl cyclocarbene as well as preparation method and application thereof

A phosphonium salt compound and compound technology applied in the field of organic synthesis to achieve high yield, mild reaction conditions and excellent catalytic activity

Inactive Publication Date: 2010-06-02
LUOYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, other heterocyclic carbene ligands (such as P-heterocycle, S-heterocycle, etc.) have also been developed rapidly. Generally, heterocyclic carbene ligands contain two or more heteroatoms, while the ring only contains one Carbene ligands with heteroatoms or even without heteroatoms are rarely reported
Up to now, only a few foreign research institutes have announced three-membered rings, six-membered rings and seven-membered ring carbocyclic carbene ligands, and there have been no reports on the cyclic (five-membered ring) carbene ligands.

Method used

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  • Phosphonium salt compound containing precursor of biphosphorus ylide cyclopentadienyl cyclocarbene as well as preparation method and application thereof
  • Phosphonium salt compound containing precursor of biphosphorus ylide cyclopentadienyl cyclocarbene as well as preparation method and application thereof
  • Phosphonium salt compound containing precursor of biphosphorus ylide cyclopentadienyl cyclocarbene as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] A phosphonium salt compound containing a bisphosphorus ylidema cyclocarbene precursor, the general formula is:

[0027] in:

[0028] R=C 6 h 5 , X=I(1); R=CH 3 , X=I(10);

[0029] R=C 6 h 5 , X=PF 6(2); R=CH 3 , X=PF 6 (11);

[0030] R=C 6 h 5 , X=Cl(3); R=CH(CH 3 ) 2 , X=PF 6 (12);

[0031] R=C 6 h 5 , X=Br(4); R=CH(CH 3 ) 2 , X=I(13);

[0032] R=C 6 h 5 , X=BF 4 (5); R=C 4 h 9 , X=I(14);

[0033] R=p-C 6 h 4 -CH 3 , X=I(6); R=C 4 h 9 , X=PF 6 (15);

[0034] R=p-C 6 h 4 -CH 3 , X=PF 6 (7); R=CH 2 CH 3 , X=I(16);

[0035] R=o-C 6 h 4 -CH 3 , X=I(8); R=CH 2 CH 3 , X=PF 6 (17);

[0036] R=o-C 6 h 4 -CH 3 , X=PF 6 (9); R=C 6 h 11 (cyclohexyl), X = I (18).

Embodiment 2

[0038] The preparation of 1,3-bistriphenylphosphine cycloiodonium phosphonium salt compound (1): add 1,1'-ferrocene dimercuric iodide (1mmol), three Phenylphosphine (2mmol), palladium chloride (0.1mmol), 20ml of anhydrous N,N-dimethylformamide, stirred and reacted for 6h at a temperature of 100°C under a nitrogen atmosphere, then filtered, and dichloromethane ( CH 2 Cl 2 ) and sherwood oil mixed solvent recrystallization to obtain the red product (1) with a yield of 36.7%. Gained product is carried out nuclear magnetic resonance analysis, data is as follows: 1 H NMR: δ=7.55-7.67 (m, 18H, Ph-H), 7.24-7.33 (m, 12H, Ph-H), 6.86 (s, 1H, C 5 h 3 ), 6.28(s, 2H, C 5 h 3 ).

Embodiment 3

[0040] The preparation of 1,3-bis-tri-p-tolylphosphine cyclohexafluorophosphate phosphonium salt compound (7): add 1,1'-ferrocene dimethyl mercury hexafluorophosphate compound in a 50ml three-necked flask equipped with a stirring reflux device (1mmol), tri-p-tolylphosphine (3mmol), palladium chloride (0.5mmol), 20ml of anhydrous N,N-dimethylformamide, stirred and reacted for 10h at a temperature of 120°C under a nitrogen atmosphere, filtered, and evaporated the solvent After using CH 2 Cl 2 Recrystallized with a mixed solvent of petroleum ether to obtain a red product (7) with a yield of 48.6%. Gained product is carried out nuclear magnetic resonance analysis, data is as follows: 1 H NMR: δ=7.36-7.52 (m, 12H, Ph-H), 7.12-7.23 (m, 12H, Ph-H), 6.92 (s, 1H, C 5 h 3 ), 6.37(s, 2H, C 5 h 3 ), 2.46(s, 18H, CH 3 ).

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Abstract

The invention relates to a phosphonium salt compound containing precursor of biphosphorus ylide cyclopentadienyl cyclocarbene as well as a preparation method and application thereof, which belong to the field of organic synthesis. The adopted technical scheme is as follows: the general formula of the phosphonium salt compound containing precursor of biphosphorus ylide cyclopentadienyl cyclocarbene: FORMULA, wherein R is alkyl or aryl, X is selected from F-, Cl-, Br-, I-, PF6-, BF4-, SbF6-, ClO4- or N3-. The preparation method of the phosphonium salt compound comprises the following steps of: adding 1, 1'-ferrocene bimercury compound, tertiary phosphine PR3 and palladium chloride to an organic solvent, refluxing under protection of N2, filtering, evaporating to dryness and recrystallizing to obtain the phosphonium salt compound. In addition, in the invention, the phosphonium salt compound is used as a catalyst ligand so that the phosphonium salt compound and the metal salt act togetherto catalyze and synthesize alpha-aryl derivatives of carbonyl compound by one step. The application test indicates that compared with traditional N-heterocyclocarbene ligand, the phosphonium salt compound has excellent catalytic activity.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a class of phosphonium salt compounds containing bisphosphorylidene cyclocarbene precursors, and the synthesis and application of the compounds. Background technique [0002] The α-aryl derivatives of carbonyl compounds (ketones, esters, amides) are important structural units of many natural products, drugs, and synthetic intermediates, and have a wide range of applications. With the development of my country's industry and economy, the demand for α-aryl derivatives of carbonyl compounds in various related industries will inevitably increase. The classic synthesis method of α-aryl derivatives of carbonyl compounds usually requires multi-step reactions, and has poor compatibility with other functional groups. Each reaction requires different arylating reagents, resulting in low yield and large amount of catalyst. defect. In recent years, the research on the α-arylation reaction ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/54B01J31/24C07B37/04C07C49/784C07C45/68C07F17/02C07C49/84C07C49/563C07C69/614C07C69/612C07C69/734C07C69/618C07C67/343
Inventor 徐晨王志强李红梅娄新华吉保明
Owner LUOYANG NORMAL UNIV
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