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Organic phosphine compound with sulfonyl functional group, as well as preparation method and application thereof

A technology of sulfonyl functional and phosphine compounds, which is applied in the field of organic phosphine compounds, can solve the problems of low synthesis efficiency, cumbersome operation, and difficulty in obtaining functional group compounds, and achieve the effect of accelerated discovery and optimization, and good technology

Inactive Publication Date: 2018-09-04
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method is cumbersome to operate, long in steps, low in synthesis efficiency, and limited by the high activity of n-butyllithium, it is difficult to obtain compounds with rich functional groups, and the compatibility of functional groups is not good, which limits the source of catalysts

Method used

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  • Organic phosphine compound with sulfonyl functional group, as well as preparation method and application thereof
  • Organic phosphine compound with sulfonyl functional group, as well as preparation method and application thereof
  • Organic phosphine compound with sulfonyl functional group, as well as preparation method and application thereof

Examples

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preparation example Construction

[0024] The preparation method of the above-mentioned organic phosphine compound with sulfonyl functional group comprises the following steps: a) reacting sulfonyl chloride with a reagent with a leaving group, introducing R 1 Functional group; b) construct carbon-phosphine bond through nucleophilic substitution reaction or coupling reaction, and introduce phosphine-containing group.

[0025] The above organic phosphine compounds having sulfonyl functional groups can be applied to the preparation of sulfonamide phosphine-containing compounds. Sulfonamide-type phosphine-containing compounds can be constructed by directly reacting nitrogen-containing nucleophiles with sulfonyl functional groups (see below). This route has mild reaction conditions and good functional group compatibility, which provides a quick way to construct a ligand library, which is much better than the prior art, and the obtained sulfonamide phosphine-containing compounds can be used as catalysts. Preferably,...

Embodiment 1

[0028] Embodiment 1 benzenesulfonyl chloride is raw material synthesis compound III

[0029]

[0030] 1. Pentafluorophenol 2-iodo-5-methylbenzenesulfonate (II) (R=I)

[0031] Pentafluorophenol and dry dichloromethane (-0.13-1 M) were added to the reaction flask, and triethylamine (2-3 equiv) was added dropwise to the solution. After stirring at room temperature for 30-120 minutes, a solution of compound III in dichloromethane (1-2 equiv, 0.5M) was added dropwise to the mixture. After the addition was complete, the reaction continued to stir at room temperature for 12-48 hours. Dichloromethane was then added for dilution, and the organic phase was washed sequentially with 1N aq HCl, 2N aq. NaOH and brine. After the obtained organic phase was dried over anhydrous sodium sulfate, the solvent was removed to obtain the white target product II with a yield of 85-90%. The test result is: 1 H NMR (400MHz, CDCl 3 )δ: 2.41(s, 3H), 7.20(d, J=8Hz, 1H), 7.87(s, 1H), 7.76(t, J=8Hz, ...

Embodiment 2

[0036] Example 2 Application of compound IV to construct sulfonamide phosphine-containing compound V

[0037]

[0038] The preparation method of compound IV is the same as that of compound III in Example 1, except that the methyl group on the benzene ring is replaced by a methoxy group.

[0039] Add triethylamine (2-4 equivalents), 1-phenylethylamine (1-2 equivalents) and 4-dimethylaminopyridine (0.1-0.5 equivalents) to IV acetonitrile solution (1-2M), then mix the mixture After stirring for 12-24 hours, the reaction temperature ranged from room temperature to reflux. After the reaction, the acetonitrile was removed, and the obtained residue was purified by column chromatography to obtain the target product V in the form of white powder.

[0040] The test result is: 1 H NMR (400MHz, CDCl 3 )δ: 1.57(d, J=6.9Hz, 3H), 3.86(s, 3H), 4.52(p, J=6.8Hz, 1H), 6.94-7.35(m, 16H), 7.60(t, J=3.0 Hz,1H); 13 C NMR(101MHz,CDCl3)δ:160.00,146.99,146.73,141.97,137.76,136.25,136.19,135.75,...

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Abstract

The invention discloses an organic phosphine compound with a sulfonyl functional group, as well as a preparation method and application thereof. The organic phosphine compound with the sulfonyl functional group comprises a sulfonyl group, a phosphine-containing group and the functional group capable of leaving through nucleophilic substitution. During preparation, sulfonyl chloride and a reagent with a leaving group are reacted, and the functional group capable of leaving through nucleophilic substitution is introduced; then a carbon phosphine bond is built through nucleophilic substitution reaction or coupling reaction, and the phosphine-containing group is introduced. The organic phosphine compound with the sulfonyl functional group provided by the invention can be subjected to nucleophilic reaction with a nucleophilic reagent so as to quickly build a ligand library, provides a favorably technology for designing and synthesizing ligands, is good for accelerating the discovery and theoptimization of the reaction, and can be applied to nucleophilic substitution reaction with the nucleophilic reagent so as to build the phosphine-containing compound.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to an organic phosphine compound with a sulfonyl functional group. Background technique [0002] Organophosphine compounds with sulfonyl functional groups show excellent catalytic performance in many reactions (Chem. Eur. J. 2015, 21, 2062-2075). In transition metal catalysis, organophosphine compounds are an important class of ligands. The activity and selectivity of the reaction are closely related to the structure and properties of the phosphine ligand. The efficient and concise synthesis of various structurally rich phosphine ligands creates favorable conditions for the optimization of the reaction. [0003] The preparation method that has been reported in the literature at present constructs the phosphine-containing compound route with sulfonamide as follows: 1. Sulfonyl chloride reacts with amine to obtain sulfonamide; 2. The hydrogen atom on the aromatic ring is taken away ...

Claims

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Application Information

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IPC IPC(8): C07F9/50
CPCC07F9/5022C07F9/5054C07F9/5068
Inventor 李乐梁大成曹小辉
Owner SUN YAT SEN UNIV
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