Photocatalytic synthesis method of thioether compound

Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a photocatalytic synthesis method of a thioether compound. The method comprises the following steps: adding a carboxylic acid compound, a non-toxic and odorless vulcanizing reagent disulfide compound, a photocatalyst and alkali into a solvent, reacting under inert gas protection and illumination conditions, and after the reaction is finished, performing post-treatment to obtain the thioether compound as shown in the formula. According to the method, reagents and substrates are simple, economical, cheap and easy to obtain, thiophenol reagents with pungent odor in a traditional process are abandoned, and a coupling reaction of C-S bonds is completed through decarboxylation by utilizing a metal-free visible light catalysis system. The method is simple in reaction operation, mild in condition, efficient in reaction and good in substrate adaptability, coupling of various substrates with different groups can be achieved, the C-S bond compound is selectively and efficiently constructed in one step, and the compound has great application prospects in medicine synthesis intermediates and has very important significance in construction of complex sulfur-containing compounds.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a photocatalytic synthesis method of sulfide compounds. Background technique [0002] As an important class of sulfur-containing functional molecules, thioethers widely exist in natural products, drugs and organic light-emitting materials. Sulfur-containing compounds can be used to treat a variety of diseases, including Alzheimer's disease, diabetes and AIDS, among others. Sulfur is present in the main skeleton of many important drug molecules, such as the commonly used antibiotic drugs penicillin and phenylprosulfone, the neurological drug barbiturate for the treatment of insomnia and anxiety, and the targeted drug enzalutamide for the treatment of prostate cancer As well as the herbicide insecticide commonly used in modern agriculture, furaquinone and so on. Therefore, it is urgent to develop an efficient and concise C-S bond construction method. [0003] For dec...

AI Technical Summary

Problems solved by technology

But use mercaptan or thiophenol as substrate, although raw material is easy to get, still there is pungent odor, and toxicity is extremely high, is not a kind of good synthetic method (J.Am.Chem.Soc., 2013,135 (25):9548-9552.)

[0005] In 2016, Fu et al. reported the arylation of thiols at room temperature, using fac-Ir(ppy)3 as a catalyst, and treating aryl thiols with cesium carbonate, resulting in the corresponding thiolate Ar 2 S-Cs + , cross-coupling with a variety of aryl halides (including iodide, bromide, and more difficultly activated chlorides and fluorides) to efficiently synthesize aryl sulfides, this method shows a wide range of resistance to various functional groups Receptivity, but the required reaction time increases (Angew.Chem.Inter.Ed.,2017,56(3):874-879.)

In the same year, Oderinde and Johannes et al. used various mercaptans and aryl / heteroaryl iodides to synthesize a variety of thioetherification products under the action of the Ir / Ni dual catalytic system. It is worth mentioning that the catalytic system is in It can still be carried out efficiently in the presence of oxygen, but the substrates are limited to aryl and heteroaryl iodides (J.Am.Chem.Soc.,2016,138(6):1760-1763.)

Images