Metal-mediated radical perfluoroalkylation of organic compounds

Barata‐Vallejo, Sebastián; Postigo, Al

doi:10.1016/j.ccr.2013.07.004

Cited by 122 publications

(28 citation statements)

References 84 publications

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“…The introduction of fluorine as the most electronegative element results in a different polarization profile of the molecule associated with improved pharmacodynamic and -kinetic properties. It is therefore not surprising that the development of a synthetic methodology for the efficient, safe, and environmentally benign preparation of these compounds by transition metal catalysis or photocatalysis has found increasing interest in the last decades [5][6][7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Visible Light-Induced Homolytic Cleavage of Perfluoroalkyl Iodides Mediated by Phosphines

et al. 2020

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In an effort to explain the experimentally observed variation of the photocatalytic activity of t Bu 3 P, n Bu 3 P and (MeO) 3 P in the blue-light regime [Helmecke et al., Org. Lett. 21 (2019) 7823], we have explored the absorption characteristics of several phosphine– and phosphite–IC 4 F 9 adducts by means of relativistic density functional theory and multireference configuration interaction methods. Based on the results of these computational and complementary experimental studies, we offer an explanation for the broad tailing of the absorption of t Bu 3 P-IC 4 F 9 and (MeO) 3 P-IC 4 F 9 into the visible-light region. Larger coordinate displacements of the ground and excited singlet potential energy wells in n Bu 3 P-IC 4 F 9 , in particular with regard to the P–I–C bending angle, reduce the Franck–Condon factors and thus the absorption probability compared to t Bu 3 P-IC 4 F 9 . Spectroscopic and computational evaluation of conformationally flexible and locked phosphites suggests that the reactivity of (MeO) 3 P may be the result of oxygen lone-pair participation and concomitant broadening of absorption. The proposed mechanism for the phosphine-catalyzed homolytic C–I cleavage of perfluorobutane iodide involves S1 ← S0 absorption of the adduct followed by intersystem crossing to the photochemically active T 1 state.

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Section: Introductionmentioning

confidence: 99%

Visible Light-Induced Homolytic Cleavage of Perfluoroalkyl Iodides Mediated by Phosphines

et al. 2020

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“…The use of aryl bromides is only very scarcely described. [8,22] This fact can be am ajor obstacle when af ourfold substitution is desired.…”

Section: Synthesis Of Double Perfluoroalkylated Corannulenesmentioning

confidence: 99%

Selective Synthesis of Perfluoroalkylated Corannulenes and Investigation of their Structural, Dynamic and Electrochemical Behavior

Haupt

Keller

Kutter

et al. 2018

Chemistry A European J

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Herein we report general methods allowing the synthesis of various perfluoroalkylated corannulenes with a specific substitution pattern. Variable temperature NMR spectroscopic investigations revealed dynamic behavior which was analyzed by line shape analysis. The activation parameters of these dynamic processes were determined. For a tetrasubstituted compound it was possible to observe through space scalar coupling. The packing motifs were elucidated by X-ray crystallography, showing that the substitution pattern as well as the size of substituents strongly influence intermolecular π-stacking. The reduction potentials of the perfluoroalkylated compounds were determined by cyclic voltammetry.

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“…Such compounds are used as surfactants [17][18][19][20], agrochemicals [21,22], pharmaceutical [23][24][25][26][27], biological [28] and medical agents [29,30]. While they are detected in human bodies [31,32], municipal water and solid wastes in different industrial areas around the world [33][34][35] and considered as high polluter for environment and toxic compounds [36,37], perfluoroalkyl acids are interesting compounds used as tensioactifs [38][39][40], fire-fighting foam [41][42][43], fluoropolymers [44] and other important applications.…”

Section: Introductionmentioning

confidence: 99%

Study of the zinc action on the 2-chloroethyl 2-bromo-2-perfluoroalkylethanoates

Yaich

Amanatoullah

Mekni

2018

Journal of Taibah University for Science

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2-Bromo-2-perfluoroalkyl acids are converted into the corresponding esters by a reaction of alcoholysis in the 2-chloroethanol. The action of zinc on perfluoroalkylated bromo-esters resulted in the bromine reduction products formation via zinc organic intermediates. When heated at 100°C, for 48 h, in the presence of an excess of zinc, the bromo-esters produce the symmetrical bis(vinyl perfluoroalkyl ester) ethoxide compounds, resulting from the BrZnF elimination reaction, followed by a dimerization reaction. ARTICLE HISTORY

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Metal-mediated radical perfluoroalkylation of organic compounds

Cited by 122 publications

References 84 publications

Visible Light-Induced Homolytic Cleavage of Perfluoroalkyl Iodides Mediated by Phosphines

Visible Light-Induced Homolytic Cleavage of Perfluoroalkyl Iodides Mediated by Phosphines

Selective Synthesis of Perfluoroalkylated Corannulenes and Investigation of their Structural, Dynamic and Electrochemical Behavior

Study of the zinc action on the 2-chloroethyl 2-bromo-2-perfluoroalkylethanoates

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