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Search for "methyl arenes" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

Benzylic C(sp³)–H fluorination

Alexander P. Atkins,
Alice C. Dean and
Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 1527–1547, doi:10.3762/bjoc.20.137

fragility of secondary and tertiary benzyl fluorides, as they observe elimination and hydrolysis in many cases [20][100], thereby raising question marks over their suitability as synthetic targets. Monofluorinated methyl arenes, however, are much more stable to these decomposition pathways. The nucleophilic

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Graphical Abstract

Figure 1: A) Benzylic fluorides in bioactive compounds, with B) the relative BDEs of different benzylic C–H b...

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Figure 2: Base-mediated benzylic fluorination with Selectfluor.

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Figure 3: Sonochemical base-mediated benzylic fluorination with Selectfluor.

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Figure 4: Mono- and difluorination of nitrogen-containing heteroaromatic benzylic substrates.

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Figure 5: Palladium-catalysed benzylic C–H fluorination with N-fluoro-2,4,6-trimethylpyridinium tetrafluorobo...

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Figure 6: Palladium-catalysed, PIP-directed benzylic C(sp³)–H fluorination of α-amino acids and proposed mech...

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Figure 7: Palladium-catalysed monodentate-directed benzylic C(sp³)–H fluorination of α-amino acids.

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Figure 8: Palladium-catalysed bidentate-directed benzylic C(sp³)–H fluorination.

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Figure 9: Palladium-catalysed benzylic fluorination using a transient directing group approach. Ratio refers ...

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Figure 10: Outline for benzylic C(sp³)–H fluorination via radical intermediates.

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Figure 11: Iron(II)-catalysed radical benzylic C(sp³)–H fluorination using Selectfluor.

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Figure 12: Silver and amino acid-mediated benzylic fluorination.

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Figure 13: Copper-catalysed radical benzylic C(sp³)–H fluorination using NFSI.

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Figure 14: Copper-catalysed C(sp³)–H fluorination of benzylic substrates with electrochemical catalyst regener...

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Figure 15: Iron-catalysed intramolecular fluorine-atom-transfer from N–F amides.

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Figure 16: Vanadium-catalysed benzylic fluorination with Selectfluor.

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Figure 17: NDHPI-catalysed radical benzylic C(sp³)–H fluorination with Selectfluor.

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Figure 18: Potassium persulfate-mediated radical benzylic C(sp³)–H fluorination with Selectfluor.

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Figure 19: Benzylic fluorination using triethylborane as a radical chain initiator.

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Figure 20: Heterobenzylic C(sp³)–H radical fluorination with Selectfluor.

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Figure 21: Benzylic fluorination of phenylacetic acids via a charge-transfer complex. NMR yields in parenthese...

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Figure 22: Oxidative radical photochemical benzylic C(sp³)–H strategies.

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Figure 23: 9-Fluorenone-catalysed photochemical radical benzylic fluorination with Selectfluor.

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Figure 24: Xanthone-photocatalysed radical benzylic fluorination with Selectfluor II.

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Figure 25: 1,2,4,5-Tetracyanobenzene-photocatalysed radical benzylic fluorination with Selectfluor.

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Figure 26: Xanthone-catalysed benzylic fluorination in continuous flow.

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Figure 27: Photochemical phenylalanine fluorination in peptides.

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Figure 28: Decatungstate-photocatalyzed versus AIBN-initiated selective benzylic fluorination.

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Figure 29: Benzylic fluorination using organic dye Acr⁺-Mes and Selectfluor.

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Figure 30: Palladium-catalysed benzylic C(sp³)–H fluorination with nucleophilic fluoride.

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Figure 31: Manganese-catalysed benzylic C(sp³)–H fluorination with AgF and Et₃N·3HF and proposed mechanism. ¹⁹...

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Figure 32: Iridium-catalysed photocatalytic benzylic C(sp³)–H fluorination with nucleophilic fluoride and N-ac...

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Figure 33: Iridium-catalysed photocatalytic benzylic C(sp³)–H fluorination with TBPB HAT reagent.

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Figure 34: Silver-catalysed, amide-promoted benzylic fluorination via a radical-polar crossover pathway.

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Figure 35: General mechanism for oxidative electrochemical benzylic C(sp³)–H fluorination.

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Figure 36: Electrochemical benzylic C(sp³)–H fluorination with HF·amine reagents.

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Figure 37: Electrochemical benzylic C(sp³)–H fluorination with 1-ethyl-3-methylimidazolium trifluoromethanesul...

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Figure 38: Electrochemical benzylic C(sp³)–H fluorination of phenylacetic acid esters with HF·amine reagents.

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Figure 39: Electrochemical benzylic C(sp³)–H fluorination of triphenylmethane with PEG and CsF.

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Figure 40: Electrochemical benzylic C(sp³)–H fluorination with caesium fluoride and fluorinated alcohol HFIP.

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Figure 41: Electrochemical secondary and tertiary benzylic C(sp³)–H fluorination. GF = graphite felt. DCE = 1,...

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Figure 42: Electrochemical primary benzylic C(sp³)–H fluorination of electron-poor toluene derivatives. Ring f...

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Figure 43: Electrochemical primary benzylic C(sp³)–H fluorination utilizing pulsed current electrolysis.

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Review

Published 10 Jul 2024

Full text

TBHP-mediated highly efficient dehydrogenative cross-oxidative coupling of methylarenes with acetanilides

Cui Chen,
Weibing Liu and
Peng Zhou

Beilstein J. Org. Chem. 2016, 12, 2250–2255, doi:10.3762/bjoc.12.217

C–N bonds. Besides, this conversion is an important complement to the conventional C–N forming strategies. Keywords: dehydrogenative cross oxidative coupling; methyl arenes; N-arylbenzamides; TBHP; Introduction Recently, amides have attracted more and more attention due to their extensive

, entries 2, 3, 5, and 9). To further extend the adaptability of this transformation, other methyl arenes were also checked under the standard conditions. Pleasingly, m-xylene and p-xylene afforded the desired product 3 successfully, but in lower yields (Table 2, entries 10 and 11). In the same manner, we

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