Oxidations involving silver—IX

Lee, J.B.; Parkin, C.; Shaw, Mukta; Hampson, N.A.; Macdonald, K. I.

doi:10.1016/0040-4020(73)80088-2

Cited by 48 publications

(13 citation statements)

References 2 publications

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“…The most promising results, however, were achieved by employing a ligand-decorated silver(II) complex: silver(II) picolinate. This complex was studied by Bacon et al in the 1960’s, 41 and was found to oxidize amines to imines (cleaved in situ to aldehydes) without extensive overoxidation. 41c It was non-basic and the oxidations were performed in water (pyrrole–imidazole alkaloids are generally stable in aqueous acidic media), making it ideal for the application to the axinellamines ( 9 – 10 ).…”

Section: Resultsmentioning

confidence: 99%

“…The originally reported synthesis of the massadines ( 11 – 12 ) 25 utilized a protected version of 25 under the assumption that oxidation of the primary amine would outcompete oxidation of C20 (as shown in Bacon’s original report). 41c However, it was found that the optimized conditions (which employed excess trifluoroacetic acid) were sufficient to completely temper the reactivity of the primary amine, allowing for the oxidation of C20 to occur in 69% yield, delivering 73 without any protecting groups. Formation of the 2-aminoimidazole was also optimized since the original report, utilizing brine as a solvent which greatly reduced the amount of Cl-OH exchange at C17, providing 72 in 65% yield.…”

Section: Resultsmentioning

confidence: 99%

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Enantioselective Total Syntheses of (−)-Palau’amine, (−)-Axinellamines, and (−)-Massadines

et al. 2011

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Dimeric pyrrole-imidazole alkaloids represent a rich and topologically unique class of marine natural products. This full account will follow the progression of efforts that culminated in the enantioselective total syntheses of the most structurally ornate members of this family: the axinellamines, the massadines, and palau’amine. A bio-inspired approach capitalizing on the pseudo-symmetry of the members of this class is recounted, delivering a deschloro derivative of the natural product core. Next, the enantioselective synthesis of the chlorocyclopentane core featuring a scalable, catalytic, enantioselective Diels–Alder reaction of a 1-siloxydiene is outlined in detail. Finally, the successful divergent conversion of this core to each of the aforementioned natural products, and the ensuing methodological developments are described.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Enantioselective Total Syntheses of (−)-Palau’amine, (−)-Axinellamines, and (−)-Massadines

et al. 2011

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“…Apart from ruthenium, copper & nickel (Section 2.1, 2.2 & 2.3), other transition metal oxidants/catalysts such as lead, silver, osmium, iridium, manganese, iron, cobalt, etc. have been reported for the ODH of amines.…”

Section: Alternative Transition Metals (Other Than Ruthenium Copper mentioning

confidence: 99%

Methods of Nitriles Synthesis from Amines through Oxidative Dehydrogenation

Patil

Gupta

2020

Adv Synth Catal

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In recent years, oxidative dehydrogenation (ODH) of amines has proven to be an efficient, clean and fundamental route for the synthesis of nitriles. This review focuses on the different types of reactions for the oxidation of amines to nitriles such as transition metal-catalysis, photoactivation, acceptorless dehydrogenation, nitroxyl radical-mediated, and N,O-doped mesoporous carbon. Emphasis is placed on the ODH of amines to the corresponding nitriles using ruthenium catalysts. Metal free systems utilizing iodine, TEMPO and its derivatives, TCCA with or without additives are also discussed. The ODH of amines using N,O-doped mesoporous carbon is elaborated. Attention is also given to major improvements, achievements, and challenges that still remain in the field of nitrile synthesis from amines. 2.3. Photocatalytic System 2.4. Acceptorless Dehydrogenation (AD) 2.5. Substrate Scope and Functional Group Tolerance 3.

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“…Die Oxidation der Aminoimidazoleinheit gelang mit Dimethyldioxiran (DMDO), ihr folgte ein nucleophiler Angriff des Guanidin-Stickstoffatoms, der den Tetracyclus 481 als Gemisch aus zwei Diastereomeren lieferte. Nach eingehenden Untersuchungen führte die C-H-Oxidation der C1-Methylengruppe mit einem Überschuss Silber(II)-picolinat (482) [231] zu einem Gemisch der gewünschten Verbindungen 483 (40 % Ausbeute aus 480). Diese wurden durch Reduktion der Azidgruppen und anschließende Verknüpfung mit zwei Brompyrroleinheiten in die Axinellamine A (485) und B (486) überführt.…”

Section: C-h-insertion Von Metallnitrenoiden (C-h-aminierung)unclassified

Funktionalisierung von C‐H‐Bindungen: neue Synthesemethoden für Naturstoffe und Pharmazeutika

2012

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Die direkte Funktionalisierung von C‐H‐Bindungen in organischen Molekülen hat sich in jüngster Zeit zu einer wirksamen und idealen Methode entwickelt, mit der Kohlenstoff‐Kohlenstoff‐ und Kohlenstoff‐Heteroatom‐Bindungen geknüpft werden können. Der Aufsatz gibt einen Überblick über die Strategien, die durch Funktionalisierung von C‐H‐Bindungen eine rasche Synthese von biologisch aktiven Verbindungen wie Naturstoffen und pharmazeutischen Zielsubstanzen ermöglichen.

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Oxidations involving silver—IX

Cited by 48 publications

References 2 publications

Enantioselective Total Syntheses of (−)-Palau’amine, (−)-Axinellamines, and (−)-Massadines

Enantioselective Total Syntheses of (−)-Palau’amine, (−)-Axinellamines, and (−)-Massadines

Methods of Nitriles Synthesis from Amines through Oxidative Dehydrogenation

Funktionalisierung von C‐H‐Bindungen: neue Synthesemethoden für Naturstoffe und Pharmazeutika

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