Silver-mediated fluorination of potassium aryltrifluoroborates with Selectfluor®

Dubbaka, Srinivas Reddy; Narreddula, Venkateswara R.; Gadde, Satyanarayana; Mathew, Thresen

doi:10.1016/j.tet.2014.10.055

Cited by 28 publications

(9 citation statements)

References 57 publications

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“…o-Ethoxyfluorobenzene 5 [26]: clear liquid, 0.74 g (59%); 1 H NMR (400 MHz, Chloroform) δ 6.86–7.11 (m, 4H), 4.11 (q, J = 7.0 Hz, 2H), 1.46 (t, J = 7.0 Hz, 3H); 13 C NMR (101 MHz, Chloroform- d ) δ 152.75 (d, J C-F = 245.25), 146.95 (d, J C-F = 10.12), 124.20 (d, J C-F = 3.89), 120.85 (d, J C-F = 7.00), 116.08 (d, J C-F = 17.91), 114.84 (d, J C-F = 1.55), 64.80, 14.75.…”

Section: Methodsmentioning

confidence: 99%

A New Alkylation of Aryl Alcohols by Boron Trifluoride Etherate

et al. 2019

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The ethylation of aryl alcohols by an ethyl moiety of boron trifluoride etherate is described. The reaction proceeded cleanly and afforded good yields of the corresponding aryl ethyl ethers. It tolerated the presence of functional groups such as aryl, alkyl, halogens, nitro, nitrile, and amino. However, the presence of amino or nitro groups ortho to a hydroxyl group of an aryl compound drastically reduced the yields of the anticipated products due to the chelation of the aforementioned functional groups with boron trifluoride etherate. A nitrogen atom in the aromatic ring system, as exemplified by hydroxypyridine and 8-hydroxyquinoline, completely inhibited the reaction. Resorcinol, hydroquinone, and aryl alcohols with aldehyde functions decomposed under the reaction conditions.

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Section: Methodsmentioning

confidence: 99%

A New Alkylation of Aryl Alcohols by Boron Trifluoride Etherate

et al. 2019

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“…The importance of fluorinated heterocyclic derivatives in the pharmaceutical and agrochemical industries continues to grow, with several fluorinated 6-membered heteroaromatic derivatives finding applications in a wide variety of drugs and plantprotective agents [15][16][17][18][19][20][21][22][23][24][25][26][27]. However, there are only a few reports on the synthesis and properties of fluorinated 5-membered heteroaromatic systems, especially those comprising two heteroatoms such as pyrazoles [28,29], isoxazoles [30], and thiazoles [31,32].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new fluorescent molecules having an aggregation-induced emission property derived from 4-fluoroisoxazoles

Sato¹,

Kawasaki²,

Karuo³

et al. 2020

Beilstein J. Org. Chem.

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Fluorescent molecules based on a fluorinated isoxazole scaffold were synthesized and investigated for their photochemical properties. The introduction of a fluorine substituent into 3,5-diarylisoxazoles led to an increase of fluorescence intensity and exhibited a redshift in the emission intensity. α-Fluorinated boron ketoiminates (F-BKIs) were also synthesized via a ring-opening reaction of 4-fluoroisoxazoles and exhibited highly fluorescent luminescence and aggregation-induced emission (AIE), showing promise as a new fluorophore.

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“…On the other hand, many fluorinated 6-membered heteroaromatic derivatives find applications in a wide variety of drugs and plant protective materials and, consequently, there are several examples of the synthesis of fluorinated 6-membered heteroaromatic rings by selective fluorination strategies. [15][16][17][18][19][20][21][22][23][24][25][26][27] However, selective fluorination of 5membered heteroaromatic systems are rare and, in particular, there are only a few reports concerning the synthesis of fluorinated 5-membered heteroaromatic systems that have two heteroatoms, such as pyrazoles [28,29], isoxaoles [30] and thiazoles [31,32]. We recently reported selective fluorination of isoxazoles to give mono-fluorinated isoxazoles (3) or tri-fluorinated isoxazolines (4) in moderate to good yields (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new fluorescent molecules having an aggregation-induced emission property derived from 4-fluoroisoxazoles

Sato¹,

Kawasaki²,

Karuo³

et al. 2020

Preprint

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Fluorescent molecules based on a fluorinated isoxazole scaffold were provided for the synthetic methods and their photochemical properties. Simple 3,5-diarylisoxazoles led to increasing the fluorescent intensity and exhibited a redshift in the emission intensity by introducing a fluorine atom. α-Fluorinated boron ketoiminates (F-BKIs) derived from a ring opening reaction of 4-fluoroisoxazoles were also synthesized and exhibited a highly fluorescent luminescence as a new aggregation-induced emission (AIE) fluorophore.

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Silver-mediated fluorination of potassium aryltrifluoroborates with Selectfluor®

Cited by 28 publications

References 57 publications

A New Alkylation of Aryl Alcohols by Boron Trifluoride Etherate

A New Alkylation of Aryl Alcohols by Boron Trifluoride Etherate

Synthesis of new fluorescent molecules having an aggregation-induced emission property derived from 4-fluoroisoxazoles

Synthesis of new fluorescent molecules having an aggregation-induced emission property derived from 4-fluoroisoxazoles

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