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Catalyst composition and use of catalyst composition or catalyst for catalyzing nucleophilic substitution reaction

A technology of catalysts and compositions, which is applied in catalytic reactions, physical/chemical process catalysts, compounds of Group 5/15 elements of the periodic table, etc., and can solve problems such as lack of reports, restrictions on large-scale use, and increased production costs

Active Publication Date: 2020-12-25
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This system requires the use of a large amount of expensive Ca(NTf 2 ) 2 , which increases the production cost, severely limits the large-scale application of this method in synthesis, and also brings inconvenience to separation and purification; at the same time, this method also lacks reports on substrates with large steric hindrance
[0005] As mentioned above, containing -SO 2 The activation of compounds of the F group has the following problems: 1) there is no broad-spectrum mild method; 2) it is necessary to use stoichiometric expensive metal salts such as Ca(NTf 2 ) 2 , is not suitable for industrial scale use and does not meet the requirements of green chemistry; 3) in the presence of -SO 2 In the reaction of F group compounds with nucleophiles, the reactivity depends heavily on the -SO 2 The chemical properties of the compound of the F group and the nucleophile, the scope of the substrate is limited

Method used

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  • Catalyst composition and use of catalyst composition or catalyst for catalyzing nucleophilic substitution reaction
  • Catalyst composition and use of catalyst composition or catalyst for catalyzing nucleophilic substitution reaction
  • Catalyst composition and use of catalyst composition or catalyst for catalyzing nucleophilic substitution reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073]

[0074] Add 3-methyl-6-(diphenylphosphine)benzenesulfonyl fluoride (0.2mmol, 1.0eq), DMSO (250μL), tert-butylamine (63.0μL, 3.0eq), HOBt (27.0mg, 1.0 eq). The reaction mixture was heated to 40°C and stirred for 24 hours. After the reaction stopped. The yield calculated by nuclear magnetic phosphorus spectrum was 87%.

Embodiment 2

[0076] Except that the catalyst HOBt was replaced by PyBOP, the reaction was carried out in the same manner as in Example 1, and the yield calculated by nuclear magnetic phosphorus spectrum was 93%.

Embodiment 3

[0078] Except that the catalyst HOBt was replaced by HOCT, the reaction was carried out in the same manner as in Example 1, and the yield calculated by nuclear magnetic phosphorus spectrum was 75%.

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PUM

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Abstract

The present invention provides a catalyst composition comprising: (a) at least one catalyst, (b) at least one silicon additive, and (c) an optional base. The invention also provides a use of the catalyst composition or catalyst according to the invention for catalyzing a nucleophilic substitution reaction of a SO2F group-containing compound with a nucleophilic agent. The catalyst or the catalyst composition according to the present invention is capable of sufficiently activating a SO2F group-containing compound and a nucleophilic reagent, thereby enabling the compound and the nucleophilic reagent to efficiently perform a nucleophilic substitution reaction. In addition, the nucleophilic substitution reaction using the catalyst composition or the catalyst is simple and convenient to operate,the yield is high, and the catalyst composition or the catalyst is suitable for large-scale production.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a catalyst composition and the use of the catalyst composition or catalyst for catalyzing nucleophilic substitution reactions. Background technique [0002] Due to its stable chemical properties and good functional group compatibility, sulfonyl fluoride plays a very important role in synthetic chemistry, and has increasingly attracted the attention of chemists and pharmacologists. Compared with sulfonyl chloride, the reaction between sulfonyl fluoride and nucleophile has disadvantages such as low efficiency and narrow substrate scope. The development of a catalyst system for activating the nucleophilic substitution reaction of sulfonyl fluoride is an important and difficult point in the field of sulfonyl fluoride research. [0003] The methods reported in the literature to activate the nucleophilic substitution reaction of sulfonyl fluoride are very limited. For example, CN 107...

Claims

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Application Information

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IPC IPC(8): B01J31/02C07B45/00C07B45/02C07B45/04C07C303/28C07C303/34C07C303/38C07D209/08C07D213/40C07D213/71C07D277/78C07D295/26C07D317/72C07D333/34C07F9/50C07C311/16C07C307/02C07C311/18C07C311/21C07C311/20C07C311/44C07C311/29C07C311/10C07C309/73
CPCB01J31/0244B01J31/0271B01J31/0274B01J31/0275B01J31/0267C07F9/5054C07C303/38C07C303/34C07D213/40C07D213/71C07D317/72C07D295/26C07D209/08C07D333/34C07B45/04C07D277/78C07C303/28C07B45/02C07B45/00B01J2231/42C07C2602/42C07C2603/70B01J35/19C07C311/16C07C307/02C07C311/18C07C311/21C07C311/20C07C311/44C07C311/29C07C311/10C07C309/73
Inventor 李乐梁大成魏明杰
Owner SUN YAT SEN UNIV
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