2016
DOI: 10.1021/acs.orglett.6b02465
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Aminofluorene-Mediated Biomimetic Domino Amination–Oxygenation of Aldehydes to Amides

Abstract: A conceptually novel biomimetic strategy based on a domino amination-oxygenation reaction was developed for direct amidation of aldehydes under metal-free conditions employing molecular oxygen as the oxidant. 9-Aminofluorene derivatives acted as pyridoxamine-5'-phosphate equivalents for efficient, chemoselective, and operationally simple amine-transfer oxygenation reaction. Unprecedented RNH transfer involving secondary amine to produce secondary amides was achieved. In the presence of O, O-amide was formed wi… Show more

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Cited by 23 publications
(11 citation statements)
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“…Therefore, the reaction proceeded through the imine/iminum ion 14 which could be formed from the condensation of amine 8 and 9H-fluoren-9-imine ( 2b ). Amine-assisted deprotonation of 14 forms the azomethine anion/ylide 15 which subsequently reacted with molecular oxygen to provide the peroxide intermediate 16 . , Related 1,2,4-dioxazolidine was known to be prepared from the reaction of α-hydroperoxy-amine with carbonyl compounds and from the reaction of carbonyl oxide with imine . Thermal disintegration of peroxide 16 provided the desired amide/lactam and 9-fluorenone. , Interestingly, imine 17b derived from benzaldehyde and benzylamine did not provide the desired amides under the standard conditions (Scheme b, eq 7).…”
Section: Results and Discussionmentioning
confidence: 99%
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“…Therefore, the reaction proceeded through the imine/iminum ion 14 which could be formed from the condensation of amine 8 and 9H-fluoren-9-imine ( 2b ). Amine-assisted deprotonation of 14 forms the azomethine anion/ylide 15 which subsequently reacted with molecular oxygen to provide the peroxide intermediate 16 . , Related 1,2,4-dioxazolidine was known to be prepared from the reaction of α-hydroperoxy-amine with carbonyl compounds and from the reaction of carbonyl oxide with imine . Thermal disintegration of peroxide 16 provided the desired amide/lactam and 9-fluorenone. , Interestingly, imine 17b derived from benzaldehyde and benzylamine did not provide the desired amides under the standard conditions (Scheme b, eq 7).…”
Section: Results and Discussionmentioning
confidence: 99%
“…To avoid this drawback, amidation reactions using catalytic amounts of coupling reagents have been developed . Additionally, conversions of alcohol and aldehyde, , oximes and nitrile, α-keto acids, and α-bromo nitroalkanes to amides were developed as alternative direct methods. However, relatively less examples were known for the direct oxidation of α-methylene group of free amines to corresponding amides because of the higher reactivity of the amine moiety.…”
Section: Introductionmentioning
confidence: 99%
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“…In order to circumvent this problem, alternative strategies toward the synthesis of amides have been explored. In recent years, oxidative amidation of aromatic aldehyde or benzyl alcohol with N , N -disubstituted formamides, amines, aminofluorenes, and 2-aminopyridines has been studied. Methylarenes as acyl donors for oxidative amidation have also been reported …”
Section: Introductionmentioning
confidence: 99%
“…11 Made from aryl alkyl carbinol. White solid; 96.3 mg, 81% yield; mp 85−87 °C; 1 H NMR (300 MHz, Chloroform-d): δ 9.02 (s, 1H), 8.40 (d, J = 8 4. Hz, 1H), 8.18 (d, J = 4.9 Hz, 1H), 7.92 (d, J = 8.2 Hz, 2H), 7.74 (t, J = 7.7 Hz, 1H), 7.54 (t, J = 6.5 Hz, 1H), 7.47 (t, J = 7.4 Hz, 2H), 7.04 (t, J = 6.2 Hz, 1H).4-Methyl-N-(pyridin-2-yl)benzamide (4) 17.…”
mentioning
confidence: 99%