392-69-8Relevant articles and documents
Selective Aryl-Fluoride Reductive Elimination from a Platinum(IV) Complex
Dubinsky-Davidchik, Ina,Goldberg, Israel,Vigalok, Arkadi,Vedernikov, Andrei N.
, p. 12447 - 12451 (2015)
A difluoro(mesityl)platinum(IV) complex underwent highly selective reductive elimination of 2-fluoromesitylene upon heating in toluene. Kinetic analysis and DFT calculations suggest that the C-F coupling involves a five-coordinate PtIV transient intermediate resulting from the rate-limiting dissociation of the pyridine ligand.
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Szele,I.,Zollinger,H.
, p. 2811 - 2815 (1978)
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Brown,de Bruyne,Gross
, p. 1291 (1934)
Photoredox catalysis with aryl sulfonium salts enables site-selective late-stage fluorination
Li, Jiakun,Chen, Junting,Sang, Ruocheng,Ham, Won-Seok,Plutschack, Matthew B.,Berger, Florian,Chabbra, Sonia,Schnegg, Alexander,Genicot, Christophe,Ritter, Tobias
, p. 56 - 62 (2019/11/28)
Photoredox catalysis, especially in combination with transition metal catalysis, can produce redox states of transition metal catalysts to facilitate challenging bond formations that are not readily accessible in conventional redox catalysis. For arene functionalization, metallophotoredox catalysis has successfully made use of the same leaving groups as those valuable in conventional cross-coupling catalysis, such as bromide. Yet the redox potentials of common photoredox catalysts are not sufficient to reduce most aryl bromides, so synthetically useful aryl radicals are often not directly available. Therefore, the development of a distinct leaving group more appropriately matched in redox potential could enable new reactivity manifolds for metallophotoredox catalysis, especially if arylcopper(iii) complexes are accessible, from which the most challenging bond-forming reactions can occur. Here we show the conceptual advantages of aryl thianthrenium salts for metallophotoredox catalysis, and their utility in site-selective late-stage aromatic fluorination.
Expanding the Balz–Schiemann Reaction: Organotrifluoroborates Serve as Competent Sources of Fluoride Ion for Fluoro-Dediazoniation
Mohy El Dine, Tharwat,Sadek, Omar,Gras, Emmanuel,Perrin, David M.
supporting information, p. 14933 - 14937 (2018/09/25)
The Balz–Schiemann reaction endures as a method for the preparation of (hetero)aryl fluorides yet is eschewed due to the need for harsh conditions or high temperatures along with the need to isolate potentially explosive diazonium salts. In a departure from these conditions, we show that various organotrifluoroborates (RBF3?s) may serve as fluoride ion sources for solution-phase fluoro-dediazoniation in organic solvents under mild conditions. This methodology was successfully extended to a one-pot process obviating aryl diazonium salt isolation. Sterically hindered (hetero)anilines are fluorinated under unprecedentedly mild conditions in good-to-excellent yields. Taken together, this work expands the repertoire of RBF3?s to act as fluorine ion sources in an update to the classic Balz–Schiemann reaction.
