Oxidative fluorination of N-arylsulfonamides

Buckingham, Faye; Calderwood, Samuel; Checa, Begoña; Keller, Thomas H.; Tredwell, Matthew; Collier, Thomas Lee; Newington, Ian M.; Bhalla, Rajiv; Glaser, Matthias; Gouverneur, Véronique

doi:10.1016/j.jfluchem.2015.07.030

Cited by 18 publications

(13 citation statements)

References 35 publications

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“…1 H NMR (600 MHz, Acetone- d 6 ) δ 10.46 (s, 1H), 8.03 (d, J = 9.4 Hz, 1H), 7.23–7.10 (m, 2H), 1.35 (s, 9H); 13 C NMR (150 MHz, Acetone -d 6 ) δ 163.1, 155.4, 132.6, 125.5, 119.0, 117.1, 36.1, 30.9; HRMS (ESI): m/z calcd for C 10 H 13 NO 3 [M—H] - 194.0823 found 194.0814; IR (Neat) ν (cm -1 ): 3233, 2967, 2907, 2871, 1622, 1588, 1530, 1481, 1438, 1369, 1324, 1277, 1228, 1208, 1178. 1 H NMR data correspond with those reported in the literature [ 14 ].…”

Section: Methodssupporting

confidence: 85%

“…1 H NMR (600 MHz, Acetone- d 6 ) δ 7.78 (d, J = 8.5 Hz, 1H), 7.32 (d, J = 1.8 Hz, 1H), 7.16 (dd, J = 8.5, 1.8 Hz, 1H), 4.00 (s, 3H), 1.37 (s, 9H); 13 C NMR (150 MHz, Acetone -d 6 ) δ 159.4, 153.4, 138.5, 125.7, 118.3, 112.0, 56.8, 36.2, 31.2; IR (Neat) ν (cm -1 ): 2971, 2873, 1604, 1589, 1522, 1493, 1466, 1450, 1406, 1363, 1311, 1287, 1243, 1207, 1190, 1164, 1084, 1026, 917, 857, 843, 826, 698, 656. 1 H NMR data correspond with those reported in the literature [ 14 ].…”

Section: Methodssupporting

confidence: 85%

“…The nitration of 5- tert -butylphenol was performed according to the procedure reported by Buckingham et al . was followed [ 14 ]. To a solution of 5- tert- butylphenol (1.5 g, 10.0 mmol) in acetic acid (7 mL) was added nitric acid (0.5 mL, 10.0 mmol) over a 5 min period (dropwise).…”

Section: Methodsmentioning

confidence: 99%

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Transetherification of 2,4-dimethoxynitrobenzene by aromatic nucleophilic substitution

et al. 2017

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In view of the few reports concerning aromatic nucleophilic substitution reactions featuring an alkoxy group as a leaving group, the aromatic nucleophilic substitution of 2,4-dimethoxynitrobenzene was investigated with a bulky t-butoxide nucleophile under microwave irradiation. The transetherification of 2,4-dimethoxynitrobenezene with sodium t-butoxide under specific conditions, namely for 20 min at 110°C in 10% dimethoxyethane in toluene, afforded the desired product in 87% yield with exclusive ortho-selectivity. A variety of reaction conditions were screened to obtain the maximum yield. The aromatic nucleophilic substitution of 2,4-dimethoxynitrobenzene with t-butoxide should be carried out under controlled conditions in order to avoid the formation of byproducts, unlike that of dihalogenated activated benzenes. Among the formed byproducts, a major compound was elucidated as 2,4-dimethoxy-N-(5-methoxy-2-nitrophenyl)aniline by X-ray crystallography.

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Section: Methodssupporting

confidence: 85%

Section: Methodssupporting

confidence: 85%

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Transetherification of 2,4-dimethoxynitrobenzene by aromatic nucleophilic substitution

et al. 2017

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“…83,84 Analogous reactions, where the iodine species is used catalytically with a secondary oxidant are known, 85,86 including enantioselective versions. 83,84,87,88 Similar reactions have been widely applied to secondary anilines and their derivatives (Scheme 6b), 89 although the products usually rearomatize by the loss of an electrofuge (e.g. tBu + , H + ).…”

Section: Cross-nucleophile Coupling Of Phenols Anilines and Amidesmentioning

confidence: 99%

Recent discoveries on the structure of iodine(iii) reagents and their use in cross-nucleophile coupling

Bauer

Maulide

2021

Chem. Sci.

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“…However, a successful para ‐selective fluorination of sulfoanilides with HF⋅Py was established by Gouverneur et al. using PIDA as the oxidant (Figure b) . More interestingly, the oxidative C−F bond formation occurred in a more beneficial way via C−C bond cleavage when the para ‐position of the anilides was substituted with a tert ‐butyl group.…”

Section: Carbon–halogen Bond Formation Reactionsmentioning

confidence: 99%

Nitrenium Ions from Amine‐Iodine(III) Combinations

et al. 2019

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Hypervalent iodine compounds are known for their extensive use as potentialo xidants in organic synthesis.I ns pite of the similar reactivity with transitionm etals,h ypervalent iodine reagents are more preferred because of their environmental sustainability.A mong several types of hypervalent iodine reagents,t rivalent organoiodine(III) reagents are highly popular due to their easy accessibility,s tability and controlled oxidizing reactivity.A lso, iodine(III) reagents are commerciallya vailable andi nexpensive. Amines and amidesr eact with iodine(III) oxidants in some specificw ay to provide ad ivalent electrophilic ionic species known as an itrenium ion. Depending on the nature and stability of the nitrenium ion, numerous oxidative transformations to generate valuable functional molecules have been reported.T his review encompassesd iscussionsa bout hypervalent organo iodine(III)-enabled organic transformationsw ith the involvemento fanitrenium ion as an intermediate. Figure1.Ionic electrophilic speciesw ith 6v alance electrons.

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Oxidative fluorination of N-arylsulfonamides

Cited by 18 publications

References 35 publications

Transetherification of 2,4-dimethoxynitrobenzene by aromatic nucleophilic substitution

Transetherification of 2,4-dimethoxynitrobenzene by aromatic nucleophilic substitution

Recent discoveries on the structure of iodine(iii) reagents and their use in cross-nucleophile coupling

Nitrenium Ions from Amine‐Iodine(III) Combinations

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