78134-79-9

Upstream product

• 811-68-7 silver(I) trifluoromethanethiolate 
• 1794-48-5 1-bromo-3-phenylprop-2-yne 
• 3355-31-5 1-chloro-3-phenyl-2-propyne 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 

Downstream Products

• 78134-80-2 1-Phenyl-3-(trifluormethansulfonyl)-propadien 
• 78134-81-3 (1S,4R,6R)-5-[1-Phenyl-meth-(E)-ylidene]-6-trifluoromethanesulfonyl-bicyclo[2.2.1]hept-2-ene 

Relevant academic research and scientific papers

FLUORINE-CONTAINING COMPOUNDS FOR USE AS NUCLEOPHILIC REAGENTS FOR TRANSFERRING FUNCTIONAL GROUPS ONTO HIGH VALUE ORGANIC COMPOUNDS

The present invention relates to a compound of general formulae (I) and their use as reagents

Perfluoroalkylation of Thiosulfonates: Synthesis of Perfluoroalkyl Sulfides

A practical synthesis of perfluoroalkyl sulfides is described. The method employs stable and readily accessible thiosulfonates as new electrophiles with commercial nucleophilic perfluoroalkylating reagents. The mild reaction conditions allow access to a wide variety of both aryl- and alkyl-substituted perfluoroalkyl sulfides amenable to pharmaceutical development. Furthermore, the reaction operation is straightforward, odorless, does not produce toxic wastes, and, therefore should appeal to practitioners in industrial-scale productions.

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.

Deoxytrifluoromethylthiolation and Selenylation of Alcohols by Using Benzothiazolium Reagents

Aliphatic compounds substituted with medicinally important trifluoromethylthio (SCF3) and trifluoromethylselenyl (SeCF3) groups were synthesized directly from alcohols by using the new benzothiazolium salts BT-SCF3 and BT-SeCF3. These bench-stable fluorine-containing reagents are facile to use and can be prepared in two steps from non-fluorinated heteroaromatic starting materials. The metal-free deoxytrifluoromethylthiolation process using BT-SCF3 proceeds under mild conditions and the similarly efficient trifluoromethylselenylation reactions using BT-SeCF3 are, to the best of our knowledge, the first reported examples of this transformation.

Regioselective dehydroxytrifluoromethylthiolation of allylic and propargylic alcohols with AgSCF3

The reaction of easily available Morita–Baylis–Hillman (MBH) alcohols with AgSCF3 in the presence of n-Bu4NI and KI affords primary allylic SCF3 products in high yields and excellent regioselectivities. This regioselective dehydroxytrifluoromethylthiolation protocol could also be extended to propargylic alcohols for the preparation of the primary propargylic SCF3 products.

Metal-Free Direct Dehydroxytrifluoromethylthiolation of Alcohols via the Umpolung Reactivity of Trifluoromethanesulfenamides

A direct dehydroxytrifluoromethylthiolation of alcohols with trifluoromethanesulfenamide has been described. This method, based on the original umpolung reactivity of trifluoromethanesulfenamides, proposes a direct "OH-SCF3 exchange" under mild and, more especially, metal-free conditions.

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.

1-PHENYL-3-(TRIFLUORMETHANSULFONYL)-PROPADIEN

For the first time a perfluoroalkanesulfonylallene, the 1-phenyl-3-(trifluoromethanesulfonyl)-propadiene (5) was synthesized. 5 is formed directly when phenylpropinyltrifluoromethanesulfide 4 is oxidized with p-nitroperbenzoic acid. 5 reacts already at ro