DBN-Mediated Addition Reaction of α-(Trifluoromethyl)styrenes with Diazoles, Triazoles, Tetrazoles, and Primary, Secondary, and Secondary Cyclic Amines

Abstract

A mild and efficient DBN-mediated addition reaction of α-(trifluoromethyl)styrenes with diazoles, triazoles, tetrazoles, and primary, secondary, and secondary cyclic amines was developed. This practical protocol provided a robust method for the synthesis of various βtrifluoromethyl nitrogen-containing heterocycles and β-trifluoromethyl amines.

Nickel-Catalyzed anti-Markovnikov Hydroalkylation of Trifluoromethylalkenes

“…Another reasonable pathway entails single electron reduction of open-shell electron poor benzylic radical intermediate IV to produce α-CF 3 carbanion V′ . Subsequent protonation of V′ would deliver product 3 (path B). ,, The significant reduction in yield with substrates bearing electron donating groups positioned para to the C–CF 3 moiety is consistent with buildup of negative charge at the benzylic position. Nonetheless, the presently available data do not allow us definitively differentiate between these C–H bond-forming pathways.…”

Metal-free photocatalytic intermolecular trifluoromethylation-gem-difluoroallylation of unactivated alkenes

“…1 Meanwhile, it is recognized that the selective installation of a trifluoromethyl (CF 3 ) group into functional organic materials and pharmaceuticals often modifies compounds with unique biological and physicochemical properties. 2 As a result, the CF 3 -involved difunctionalization of alkenes has attracted significant attention in the last few years, and useful approaches such as carbo-trifluoromethylation, 3 amino-trifluoromethylation, 4 thio-trifluoromethylation, 5 oxy-trifluoromethylation 6 and halo-trifluoromethylation 7 have provided single-step direct access to a variety of valuable and complicated trifluoromethylated compounds by using either a photocatalyst or transition metal catalyst (Scheme 1a). 8 Despite these impressive achievements, the scope of CF 3 -involved difunctionalization is still limited, and a method enabling the simultaneous introduction of a trifluoromethyl group and other functional groups is highly desirable.…”

Solvent-controlled base-free synthesis of bis(trifluoromethyl)-cyclopropanes and -pyrazolines via cycloaddition of 2-trifluoromethyl-1,3-enynes with 2,2,2-trifluorodiazoethane

“…1 Therefore, considerable efforts have been focused on developing efficient strategies for the incorporation of a CF 3 group into organic compounds by using various trifluoromethylating reagents and trifluoromethyl-containing building blocks. 2 Recently, 2,2,2-trifluorodiazoethane (CF 3 CHN 2 ) and 2-trifluoromethyl-1,3-conjugated enynes have emerged as attractive CF 3 sources for the construction of CF 3 -containing compounds due to their high reactivity and ready availability. 3,4 Consequently, extensive attention has been devoted toward the development of new reactions of these two valuable CF 3 -containing building blocks.…”