A new application of (polyfluoroorgano)trifluoroborate salts: the palladium-catalysed cross-coupling reaction with substituted benzenediazonium tetrafluoroborates

Frohn, Hermann‐Josef; Adonin, Nicolay Yu.; Bardin, V. V.; Starichenko, V. F.

doi:10.1016/s0022-1139(02)00157-4

Cited by 52 publications

(25 citation statements)

References 23 publications

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“…2,3,4′,5,6‐Pentafluoro‐1,1′‐biphenyl (3v): 12 Yield: 46.4 mg (76%); colorless solid; 1 H NMR (400 MHz, CDCl 3 ): δ =7.47–7.43 (m, 2 H), 7.19 (t, J =8.2 Hz, 2 H), 7.12–7.03 (m, 1 H); 13 C NMR (100 MHz, CDCl 3 ): δ =163.1 (d, J =248.2 Hz), 147.6–147.3 (m), 145.2–144.9 (m), 142.6–142.4 (m), 132.1–132.0 (m), 123.3, 120.5, 115.8 (d, J =21.7 Hz), 105.0.…”

Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Desulfitative Direct CH Arylation of Electron‐Deficient Polyfluoroarenes with Sodium Arenesulfinates

Miao

Wang

2013

Adv Synth Catal

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The palladium-catalyzed direct arylation of electron-deficient polyfluorobenzenes was developed in the presence of silver carbonate and trisodium phosphate. This protocol allowed use of both electron-deficient and electron-rich aromatic sulfinic acid sodium salts as arylating reagents for the direct arylation of a variety of polyfluoroarenes to produce fluorobiaryls in good to excellent yields, providing a complement to the existing methods for the direct arylation of polyfluoroarenes.

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Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Desulfitative Direct CH Arylation of Electron‐Deficient Polyfluoroarenes with Sodium Arenesulfinates

Miao

Wang

2013

Adv Synth Catal

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“…Most of the methods for the synthesis of polyfluorinated diaryls were needed transition metal, usually palladium or copper, as well as regularly used organometallic starting materials, for example boronic acids, borate salts,, copper species, or stannanes (Scheme a ) . In 2016, the metal‐free, visible light induced perfluoroarylation of (hetero)arenes with fluorinated bromoarenes using an organic photoredox catalyst with the aid of triethylamine was reported by the research group of König (Scheme b ) .…”

Section: Using Non‐metal Catalysismentioning

confidence: 99%

Recent Developments in Radical‐Mediated Transformations of Organohalides

Lekkala

Balakrishna

et al. 2019

Eur J Org Chem

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In recent years, radical‐mediated transformations of organohalides, a class of powerful chemical transformations, have become an important field at the forefront of organic chemistry. Formation of free‐radicals from organohalides is among the most useful methods to access open‐shell reactive intermediates that have a number of established applications in chemical synthesis. Herein we summarize most of the strategies involving metal‐catalyzed, non‐metal‐catalyzed, as well as catalyst‐free radical‐mediated transformations of organohalides.

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“…144 These lower yields of biaryls compared with those obtained with non-fluorinated aryltrifluoroborates may be attributed to the lower reactivity of K[C 6 F 5 BF 3 ] and to its sensitivity to hydrodeboration. In another example, 144 the authors showed that (trifluoroethenyl)trifluoroborate, the fluorous analogue of vinyltrifluoroborate, could also couple with diazonium salts, even in lower yields (Scheme 79). This later example represents the first coupling of a perfluoroalken-1-yl organometallic reagent catalyzed by a transition metal.…”

Section: Cross-coupling With Arenediazonium Saltsmentioning

confidence: 99%