Trifluoromethylated compounds are of great importance in the areas of pharmceuticals and agrochemicals. We can see many notable pharmaceutical compounds containing a trifluoromethyl group on the market, such as:Fluoxetine, Mefloquine, Leflunomide, Nulitamide, Dutasteride, Bicalutamide, Aprepitant, Celecoxib, Fipronil, Fluazinam, Penthiopyrad, Picoxystrobin, Fluridone, Norflurazon, Sorafenib and Triflurazin.
Compared to mono-and difluoromethylation,fewer synthesis strategies are available for the introduction of CF3 group into organic molecules, becuase three of the four substituents on the carbon atom are pre-determined which limits potential synthetic handles. but trifluoromethylation has still become a rapidly growing field in chemical research with significant advances made in the past decades,either stoichiometric or catalytic reagents.
For nucleophilic trifluoromethylation with CF3− anion as active species, the Ruppert-Prakash reagent( TMSCF3,kumi3F01) has long been a versatile source for incorporating a trifluoromethyl group to target compounds, although it is a hydrolyzable, moisture sensitive liquid. Some new weighable, crystalline nucleophilic reagents have been developed accordingly. For example, the Colby trifluoromethylation reagent(kumi6F01) is an air-stable solid that adds CF3 group to ketones and thiols under mild reaction conditions with enviromental friendly side-products.
For radical trifluoromethylation with trifluoromethyl free radical as active species, the use of solid and bench-top stable reagent(NaSO2CF3,kumi3F19) was first described by Langlois for the radical trifluoromethylation of electron-rich arenes. The Baran group has later developed a improved radical trifluoromethylation with TFMS Reagent (Zn(SO2CF3)2 , kumi6F04) to transformer aryl and herteroaryl C-H bonds directly to C-CF3) bonds under mild conditions. The Trifluoromethylator® ((Phen)Cu-CF3),kumi3F18),developped by the Hartwig group, is an easily handled, thermally stable, single-component reagent for adding the CF3 moiety to aryl iodide and aryl bromide; its wide applicability was also demonstrated by reacting heteroaryl bromide and iodides with various functional groups, giving the desired products in good-to-high yields.
For electrophilic trifluoromethylationwith CF3+ cation as active species, a range of substrates can be trifluoromethylated employing functional group tolerant reagents and conditions.Many widely used crystalline electrophilic trifluoromethylating reagents have been developped,especaily preferable for laboratory settings. Notably, the Togni(kumi3F10) and Togni II(kumi3F11) reagents can provide highly-selective,direct,mild and efficient trifluoromethylation of a wide range of substrates; both reagents are offered safer alternatives for shipment and storage. Very recently, Umemoto's Reagents(kumi8F02,kumiAF01,kumiBF01) were developped as a family of powerful, shelf-stable electronphilic trifluoromethylating toolkits, applicable to various nucleophiles( e.g. ß-ketoeasters,Indoles and Phosphines,etc.).
Kumidas offers the above-mentioned three classes of reagents amendable to trifluoromethylation either in stoichiometric or catalytic amounts,which will take you seemlessly from discovery to R&D with faster time-to-market.
Trifluoromethylating Reagents Overview
(Click each block for more information on individual product)
You can either buy our trifluoromethylating reagents and then introduce trifluoromethylated moiety into your own desired compounds, or you can simply order the building blocks pre-loaded with the -CF3 subsitituent.
For more information about additional trifluoromethyl building blocks, please contact us by sending email to firstname.lastname@example.org.