Photocatalytic fluoroalkylation reactions of organic compounds

Abstract

Photocatalytic methods for fluoroalkyl-radical generation provide more convenient alternatives to the classical perfluoroalkyl-radical (Rf) production through chemical initiators, such as azo or peroxide compounds or the employment of transition metals through a thermal electron transfer (ET) initiation process.

Mechanism and Applications of the Photoredox Catalytic Coupling of Benzyl Bromides

“…[38][39][40][41][42][43][44][45][46][47][48][49][50][51][52][53][54] We have also explored photoredox catalysis employing photofunctional complexes of Ru II ,I r III ,a nd Pt II ,a nd established the photoelectrochemical mechanismso ft he reductive actions of such complexes. Radical species canb ed erived from benzylh alidest hrough photoinduced reductived issociation.…”

“…Indeed,p hotoredox catalysis mediated by the transition-metal complexes has been demonstrated in aw ide range of organic transformations. [38][39][40][41][42][43][44][45][46][47][48][49][50][51][52][53][54] We have also explored photoredox catalysis employing photofunctional complexes of Ru II ,I r III ,a nd Pt II ,a nd established the photoelectrochemical mechanismso ft he reductive actions of such complexes. [55][56][57][58][59][60] Ta king advantage of ourm echanisticu nderstanding, we set out to explore the utility of this photoinduced radical generation strategy in the bibenzyl synthesis.…”

Benign Perfluoroalkylation of Aniline Derivatives through Photoredox Organocatalysis under Visible‐Light Irradiation

“…tion (HAS). [6] The HAS reaction with the CF 3 group has been well documented; [7] however, fewer examples have been reported for HAS perfluoroalkylation. [8][9][10][11] HAS reactions with perfluoroalkyl groups can be performed by two methods: thermal and photoinduced.…”

Visible Light Photocatalytic Radical Addition/Cyclization Reaction of o‐Vinyl‐N‐Alkoxybenzamides for Synthesis of CF3‐Containing Iminoisobenzofurans

“…In particular, iminoisobenzofurans have recently become increasingly attractive synthetic targets. [1,11] On the basis of our continued interest in the photoredox-catalyzed synthesis of heterocycles, [4,12] herein, we disclosed a visible light-driven photocatalytic radical addition/cyclization of o-vinyl-N-alkoxybenzamides (Scheme 1b). [10] Despite these advances, to our knowledge, there is no report on the practical, general, and catalytic synthesis of fluoroalkylated iminoisobenzofurans.…”

“…On the basis of these mechanistic studies and related literature, [11] we proposed a plausible redoxneutral process for the current photocatalytic radical addition/cyclization reaction (Scheme 4). First, a single electron transfer from the excited state photocatalyst *[Ru(bpy) 3 ] 2 + , formed reversibly upon visible light 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 irradiation, to the Umemoto reagent 2 a occurs to generate the highly reactive CF 3 radical and the oxdized form of the photocatalyst [Ru(bpy) 3 ] 3 + .…”