Fluoroalkylation reactions in aqueous media: a review

Abstract

Recent advances in aqueous fluoroalkylation using various fluoroalkylation reagents are summarized in this review.

Integrated redox-active reagents for photoinduced regio- and stereoselective fluorocarboborylation

“…ifunctionalization of alkenes and alkynes has been widely explored for rapid diversification of double/triple bonds [1][2][3][4][5][6] . Traditional transition metal-catalyzed difunctionalization methods have been well-developed to control the regioselectivity and stereoselectivity 7,8 .…”

Markovnikov-Type Hydrotrifluoromethylchalcogenation of Unactivated Terminal Alkenes with [Me4N][XCF3] (X = S, Se) and TfOH

“…Recently, the special stereoelectronic and physicochemical properties originating from the association of the trifluoromethyl (CF 3 ) moiety with chalcogens (e.g., oxygen, sulfur and selenium) have been well documented [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 ]. The OCF 3 and SCF 3 groups possess strong electronegativity, considerable steric hindrance, and high lipophilicity, which can significantly change the bioactivity of a molecule [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 ]. The least-studied SeCF 3 group represents another important functionality, exhibiting a valuable stereoelectronic nature and lipophilicity, and has immense potential to modulate the potency of agrochemicals and pharmaceuticals [ 11 , 12 , 13 ].…”

“…Although selenium substances have shown very useful biological activities and have been widely utilized in drug design and development [ 14 , 15 , 16 , 17 , 18 ], to our knowledge, the uses of SeCF3-containing compounds have rarely been explored in comparison with those non-fluorinated analogues. This may be attributed to the lack of structural diversity, sufficient synthetic methods, and imperative biological investigation of the trifluoromethylselenolated compounds [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 ]. Thus, continuously developing efficient approaches for the construction of different types of SeCF 3 -containing organic scaffolds for future function studies is highly sought-after.…”

Perfluoroalkylative pyridylation of alkenesvia4-cyanopyridine-boryl radicals

“…In particular, building two C–C bonds tandemly in a single step is highly deserved in terms of structure diversity, step and atom economy. Incoporation of a perfluoroalkyl group in this tandem reaction would be attractive with potential applications in medicinal chemistry, agrochemistry, materials science 2. Along this line, radical-mediated perfluoroalkylative difunctionalization of alkenes, through transition-metal catalysis,3 photoredox catalysis,4 or visible-light activation of electron donor–acceptor (EDA) complexes,5 has played privileged roles in these transformations (Scheme 1, up).…”