Trifluoromethylthiolation Agents

Trifluoromethylthiolation Agents

Introduction

Trifluoromethylthiolation agents can directly introduce trifluoromethylthio groups into the molecules without pre-preparing sulfur-containing compounds. Trifluoromethylthio groups have high fat solubility and strong electron-withdrawing ability. The introduction of trifluoromethylthio groups into organic molecules can change the molecular pharmacokinetics and physicochemical properties, and improve metabolic stability. Therefore, molecules containing trifluoromethylthio groups have been widely used in the fields of medicine, pesticides, materials, and fluorine-containing daily necessities. As a reagent for the efficient synthesis of trifluoromethylthio compounds, trifluoromethylthiolation agents provide a convenient and concise method for introducing trifluoromethylthio groups, and the conditions are mild and the functional group compatibility is good.

Classification

Based on the electrical effect of the compound, trifluoromethylthiolation agents are divided into nucleophilic trifluoromethylthiolation agents, electrophilic trifluoromethylthiolation agents and free radical trifluoromethylthiolation agents.

• Nucleophilic trifluoromethylthiolation agents. Nucleophilic trifluoromethylthiolation agents mainly include trifluoromethylthio metal salts, such as AgSCF₃, CuSCF₃, and trifluoromethylthio tetraalkylammonium ((NR₄)SCF₃). Under the catalysis of transition metals, many nucleophilic trifluoromethylthiolation agents can undergo coupling reactions with halogenated arenes, or introduce trifluoromethylthio groups through C-H activation under the induction of directing groups.
• Electrophilic trifluoromethylthiolation agents. Electrophilic trifluoromethylthiolation agents are easy-to-operate and stable. They can realize electrophilic trifluoromethylthiolation reactions of various types of substrates, such as electron-rich aromatic hydrocarbons, heteroaromatic hydrocarbons, alcohols, thiols, amines, terminal alkynes, olefins, aldehydes, ketones and carboxylic acids. The common ones are Billard reagent, Munavalli reagent, Shibata reagent, N-trifluoromethylthiodiimide reagent, N-trifluoromethylthiobisbenzenesulfonimide reagent, Shen reagent and so on. In addition, a novel electrophilic trifluoromethylthiolation agent, N-trifluoromethylthiosaccharin, which has better reactivity, can react with many nucleophiles under mild conditions to obtain the corresponding trifluoromethylthiolated products in good yields, and the reaction rate is very fast.
• Free radical trifluoromethylthiolation agents. Free radical trifluoromethylthiolation agents usually generate trifluoromethylthio free radicals under oxidative or light conditions, followed by a free radical tandem reaction with the substrate. The most widely used are AgSCF₃, N-trifluoromethylthiophthalimide, N-trifluoromethylthiosuccinimide.

Alfa Chemistry can offer various trifluoromethylthiocarbonylation agents, including nucleophilic trifluoromethylthiocarbonylation agents, electrophilic trifluoromethylthiocarbonylation agents and free radical trifluoromethylthiocarbonylation agents. You can click on our product list for a detailed view. If you do not find the product you want, we also offer product customization according to customer's detailed requirements. Please contact us, if you are in need of assistance.