Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for generating C-S bond by decarboxylating active ester compound

An ester compound, C-S technology, applied in the direction of organic chemistry, sulfide preparation, etc., can solve the problem of limited sulfur source, and achieve the effect of high reactivity and easy preparation

Active Publication Date: 2021-09-17
HAINAN NORMAL UNIV
View PDF1 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in existing decarboxylation methods for building C-S bonds, sulfur sources are limited to thiols or thiophenols

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for generating C-S bond by decarboxylating active ester compound
  • Method for generating C-S bond by decarboxylating active ester compound
  • Method for generating C-S bond by decarboxylating active ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In this embodiment, several treatment groups are set based on the following comparison treatment methods. Except for the description of special variables, the treatment methods of each treatment group are strictly consistent with the comparison treatment methods. The reaction formula is as follows:

[0021]

[0022] In the reactants used in the control treatment, as active ester, with as a sulfur source.

[0023] Control treatment method: 0.1 mmol of 0.2mmol 0.2 mmol of N,N-diisopropylethylamine was added to 1 mL of dimethylacetamide (DMAc), and the photocatalyst Ru(bpy) was added to the reactant in an amount of 1 mol%. 2 Cl 2 ·6H 2 O; at room temperature, provide blue light illumination, and react for 20 hours.

[0024] The variable settings of each treatment group and the yield of the target product are shown in Table 1.

[0025] Table 1 Influence of the setting mode of each treatment group in the present embodiment on the yield of the target product

...

Embodiment 2

[0030] In this embodiment, a variety of general formulas are selected as R a -The active ester of COONPhth and the general formula are As a reactant (in the present embodiment, X is a C atom or a N atom), the decarboxylation coupling reaction is carried out according to the following steps:

[0031] Put 0.2 mmol of R a -COONPhth, 0.4 mmol 0.4 mmol of DIPEA was added to 1 mL of DMAc, and the photocatalyst Ru(bpy) was added to the reactant according to the addition amount of 1 mol% 2 Cl 2 ·6H 2 O; at room temperature, provide blue light illumination, and react for 20 hours. The reaction formula is as follows:

[0032]

[0033] Each group of reactants used in this example and their corresponding target products are shown in Table 2.

[0034] Table 2 Reactants and their corresponding target products

[0035]

[0036]

[0037] After the reaction, the product yields of various target products were counted, as shown in Table 3.

[0038] According to Table 2 and Ta...

Embodiment 3

[0043] In this embodiment, the general formula is amino acid active esters and As a reactant, the decarboxylation coupling reaction was carried out according to the following steps:

[0044] will be 0.2 mmol 0.4mmol 0.4 mmol of DIPEA was added to 1 mL of DMAc, and the photocatalyst Ru(bpy)2Cl2·6H2O was added to the reactant according to the addition amount of 1 mol%; at room temperature, the reaction was performed for 20 hours under blue light illumination. The reaction formula is as follows:

[0045]

[0046] Each group of reactants used in this example and their corresponding target products and product yields are shown in Table 4. All the tested amino acid active esters in this example can obtain the target product by performing the above reaction, and the yield of the target product can reach a moderate to excellent grade. As shown in Table 4, phenylalanine (corresponding product 15), leucine (corresponding product 16), valine (corresponding product 17), alanin...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

One aspect of the invention provides a method for generating a C-S bond by decarboxylating an active ester compound. The method comprises the following steps: under an illumination condition, active ester with a general formula of Ra-COONPhth and disulfide with a general formula of Rb-S-S-Rc are subjected to the following reaction: Ra-COONPhth + Rb-S-S-Rc -> Ra-S-Rb in a liquid environment provided by an organic solvent containing organic alkali under the catalysis of a photocatalyst, wherein in Ra-S-Rb, Ra and S atoms are bonded through C-S, the photocatalyst is Ru(bpy)2Cl2.6H2O, and Rb and Rc are independently selected from one of alkyl, optionally substituted alkyl, polyheterocycle or optionally substituted polyheterocycle, and both Rb and Rc are aromatic groups. The selectable range of reactants in the reaction is wide, and alkyl sulfides with various structures can be prepared through the reaction.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a method for generating C-S bonds by decarboxylation of active ester compounds. Background technique [0002] C-S bonds widely exist in many common biologically active substances, natural products and functional materials. Especially in the field of medicinal chemistry, sulfur-containing organic compounds play an important role in disease types such as cancer, diabetes, Alzheimer's disease and AIDS. Therefore, how to construct C-S bonds conveniently and efficiently is of great significance in synthetic chemistry. [0003] Over the past few decades, efforts have been made to utilize transition metal catalysis to construct C–S bonds, including the cross-coupling of aryl halides or borates with thiols or disulfides, and the synthesis of S–S and S–H bonds with alkyne triple bonds. addition reaction. In recent years, photoredox catalysis has emerged as a powerful and pr...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C07C323/22C07D333/22C07D211/54C07D307/18C07C323/59C07D213/70C07C323/43C07D207/12C07D209/14C07D333/34
CPCC07C319/14C07D333/22C07D211/54C07D307/18C07D213/70C07D207/12C07D209/14C07D333/34C07C2601/02C07C2601/14C07C323/22C07C323/59C07C323/43Y02P20/584
Inventor 郑超王璐肖智伟谭海波李小宝陈光英魏俊杰
Owner HAINAN NORMAL UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com