2015
DOI: 10.1021/acs.joc.5b00857
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Selectfluor-Mediated Simultaneous Cleavage of C–O and C–C Bonds in α,β-Epoxy Ketones Under Transition-Metal-Free Conditions: A Route to 1,2-Diketones

Abstract: Selectfluor-mediated simultaneous cleavage of C-O and C-C bonds in α,β-epoxy ketones has been successfully achieved under transition-metal-free conditions. The reaction gives 1,2-diketone compounds in moderate to good yields involving a ring-opening/benzoyl rearrangement/C-C bond cleavage sequence under oxidative conditions.

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Cited by 27 publications
(11 citation statements)
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“…Benzil: 1 H NMR (400 MHz, CDCl 3 ): δ = 7.97 (d, J = 7.5 Hz, 2 H), 7.65 (t, J = 7.5 Hz, 2 H), 7.50 (t, J = 7.5 Hz, 4 H) ppm. 13 C NMR (100 MHz): δ = 194.7, 135.0, 133.0, 130.0, 129.1 ppm.…”
Section: Methodsmentioning
confidence: 99%
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“…Benzil: 1 H NMR (400 MHz, CDCl 3 ): δ = 7.97 (d, J = 7.5 Hz, 2 H), 7.65 (t, J = 7.5 Hz, 2 H), 7.50 (t, J = 7.5 Hz, 4 H) ppm. 13 C NMR (100 MHz): δ = 194.7, 135.0, 133.0, 130.0, 129.1 ppm.…”
Section: Methodsmentioning
confidence: 99%
“…1‐Phenyl‐2‐ p ‐tolylethane‐1,2‐dione: 1 H NMR (400 MHz, CDCl 3 ): δ = 7.97 (d, J = 7.5 Hz, 2 H), 7.87 (d, J = 7.5 Hz, 2 H) 7.65 (t, J = 5.8 Hz, 1 H), 7.51 (t, J = 7.5 Hz, 2 H), 7.31 (d, J = 7.5 Hz, 2 H), 2.44 (s, 3 H) ppm. 13 C NMR (CDCl 3 , 100 MHz): δ = 194.9, 194.5, 146.4, 134.9, 133.2, 130.7, 130.2, 130.0, 129.9, 129.1, 22.1 ppm.…”
Section: Methodsmentioning
confidence: 99%
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“…Based on literature precedent, catalysts generally categorized into phase transfer catalyst, metal/transition metals and enzyme and protein based catalyst ( Fig. 1) [88][89][90][91][92][93][94][95][96][97][98].…”
Section: Type Of Catalystsmentioning
confidence: 99%
“…Protonation reactions of free-base pyridylporphyrins possessing mixed meso-pyridyl and meso-4-aminophenyl groups were also examined by Wamser and coworkers, with the progress of the reaction being monitored, in this case by both UV/Visible [11] and NMR spectroscopy. [32] An interaction was shown to occur between a meso-aminophenyl group of one porphyrin and a protonated pyridyl group or coreprotonated nitrogen of another porphyrin, but no such interaction was present for the free-base pyridyl porphyrins lacking aminophenyl groups at the other meso-positions of the macrocycle.…”
Section: Introductionmentioning
confidence: 99%