1464149-40-3

Upstream product

• 4392-24-9 Cinnamyl bromide 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 104-54-1 3-Phenylpropenol 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 811-68-7 silver(I) trifluoromethanethiolate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 104713-12-4 (R)-1-phenylprop-2-en-1-ol 
• 160879-62-9 methyl 1-phenylprop-2-enyl carbonate 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 

Downstream Products

• 40032-55-1 N-cinnamylbenzylamine 
• 104937-80-6 N-(1-phenyl-2-propenyl)benzylamine 
• 119793-72-5 (E)-2-(3-phenyl-allyl) malonic acid dimethyl ester 
• 87802-78-6 dimethyl 2-(1-phenylallyl)malonate 

Relevant academic research and scientific papers

Trifluoromethyl sulfoxides from allylic alcohols and electrophilic SCF3 Donor by [2,3]-sigmatropic rearrangement

An electrophilic trifluoromethylthiolation of allylic alcohols produces the corresponding allylic trifluoromethanesulfenates, which spontaneously rearrange into trifluoromethyl sulfoxides via a [2,3]-sigmatropic rearrangement. The reaction is straightforward and proceeds in good to high yields for the preparation of various allylic trifluoromethyl sulfoxides.

Dehydroxylative Trifluoromethylthiolation, Trifluoromethylation, and Difluoromethylation of Alcohols

CF3S, CF3 and HCF2 groups have been identified as valuable functionalities for drug development. Despite significant accomplishments in the trifluoromethylthiolation, trifluoromethylation and difluoromethylation reactions, directly converting common functional groups into CF3S, CF3 or HCF2 groups is still highly desirable. Described here is the dehydroxylative trifluoromethylthiolation, trifluoromethylation and difluoromethylation of alcohols promoted by a R3P/ICH2CH2I system. All of these dehydroxylative reactions were achieved under mild conditions via the activation of the hydroxyl group by the R3P/ICH2CH2I system. A wide substrate scope and good functional group tolerance were observed.

Ionic Liquids for Fast and Solvent-Free Nucleophilic Trifluoromethylthiolation of Alkyl Halides and Alcohols

The trifluoromethylthio group is of rising interest in medicinal, agrochemical, and materials chemistry. Although several strategies for the introduction of this functional group have been described, new synthetic methods are needed. A novel ionic liquid, 1-n-butyl-3-methylimidazolium trifluoromethylthiolate, has been developed and is herein reported as an efficient and recyclable in situ generated trifluoromethylthiolating reagent for alkyl halides, sulfonates, and even unactivated alcohols under solvent-free conditions.

Copper(I)-mediated direct trifluoromethylthiolation of allylic halides with elemental sulfur and (trifluoromethyl)trimethylsilane

Abstract A new method has been developed for the copper-mediated trifluoromethylthiolation of allylic halides by using potassium fluoride, elemental sulfur, and (trifluoromethyl)trimethylsilane in anhydrous N,N-dimethylformamide. This protocol provides facile access to a variety of allylic trifluoromethyl thioethers in moderate to good yields under mild, ligand-free reaction conditions.

Metal-Free Trifluoromethylthiolation of Alkyl Electrophiles via a Cascade of Thiocyanation and Nucleophilic Cyanide-CF3 Substitution

A straightforward synthesis of alkyl trifluoromethyl thioethers was developed that starts from widely available alkyl halides or mesylates and the inexpensive reagents sodium thiocyanate and trimethyl(trifluoromethyl)silane. The alkyl electrophiles are converted in situ into the corresponding thiocyanates, which react with the nucleophilic Ruppert-Prakash reagent to give the corresponding trifluoromethyl thioethers via a Langlois-type CN-CF3 substitution. This process enables the efficient introduction of the pharmaceutically meaningful trifluoromethylthio groups into functionalized molecules without the need of metal catalysts or expensive preformed trifluoromethylthiolating agents.

Direct dehydroxytrifluoromethylthiolation of alcohols using silver(I) trifluoromethanethiolate and tetra-n-butylammonium iodide

An unprecedented reaction for the direct trifluoromethylthiolation and fluorination of alkyl alcohols using AgSCF3 and nBu4NI has been developed. The trifluoromethylthiolated compounds and alkyl fluorides were selectively formed by c

Synthesis of allylic and propargylic trifluoromethyl thioethers by copper(i)-catalyzed trifluoromethylthiolation of allylic bromides and propargylic chlorides

An efficient method is reported for the copper(I)-catalyzed trifluoromethylthiolation of allylic bromides by using elemental sulfur and CF3SiMe3. This rate of this transformation was significantly accelerated in the presence of 18-crown-6, and the reaction afforded the desired products in moderate to excellent yields with high stereo- and regioselectivity. This method can tolerate a number of functional groups and provides facile access to a variety of allylic trifluoromethyl thioethers. The copper(I)-catalyzed trifluoromethylthiolation of propargylic chlorides was also investigated. A plausible mechanism that involves an allylcopper(III) intermediate is proposed.

Ruthenium-catalyzed regioselective allylic trifluoromethylthiolation reaction

An efficient Ru-catalyzed regioselective allylic trifluoromethylthiolation reaction of allylic carbonates was developed. The linear allylic trifluoromethyl thioethers were obtained in 52-91% yields. Mechanistic investigation revealed that this reaction proceeds via a double allylic trifluoromethylthiolation sequence.

Copper(I) trifluoromethylthiolate complex bearing triphenylphosphine ligand for nucleophilic trifluoromethylthiolation of allylic bromides

Copper(I) trifluoromethylthiolate complex (PPh3) 2Cu(SCF3) (1) has been synthesized from a convenient reaction of CuF2 with CF3SiMe3 and S 8 in the presence of triphenylphosphine. The crystal structure of complex 1 has been determined by X-ray crystallography. In the solid state, complex 1 exists as a monomeric copper(I) species with a three-coordinated trigonal planar geometry. Complex 1 reacted with a wide range of allylic bromides to afford corresponding allylic trifluoromethyl thioethers in moderate to good yields. Several functional groups, including alkyl, alkoxy, nitro, halides and geranyl groups, are tolerated.

Nucleophilic trifluoromethylthiolation of allylic bromides: A facile preparation of allylic trifluoromethyl thioethers

A facile preparation of allylic trifluoromethyl thioethers was achieved by using a copper reagent. The reaction of (bpy)Cu(SCF3) with various allylic bromides afforded the desired trifluoromethylthiolation products in good to excellent yields with high stereo- and regioselectivity. Common functional groups such as alkyl, alkoxy, trifluoromethyl, nitro, halides and geranyl are well tolerated. A facile preparation of allylic trifluoromethyl thioethers was achieved by the reaction of (bpy)Cu(SCF3) with allylic bromides. This protocol afforded the desired trifluoromethylthiolation products in good to excellent yields with high stereo- and regioselectivity. Important functional groups such as alkyl, alkoxy, trifluoromethyl, nitro, halides and geranyl are well tolerated. Copyright