Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl–Olefin Metathesis

McAtee, Christopher C.; Riehl, Paul S.; Schindler, Corinna S.

doi:10.1021/jacs.7b01114

Cited by 124 publications

(81 citation statements)

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“…4 Recently, in an effort to enhance the synthetic utility of carbonyl-olefin metathesis, our group has reported a catalytic variant of this reaction which relies on FeCl 3 as an environmentally benign and economically sustainable catalyst, which was followed by a report from Li and coworkers. 5 While our previously reported catalytic carbonyl-olefin metathesis strategy has proven useful toward the synthesis of many cyclic scaffolds including cycloalkenes, 5,6 polycyclic aromatic hydrocarbons, 7 and azacycles, 8 we anticipate that a theoretical and experimental investigation of the reaction mechanism can provide insight which will lead to further improvements in the reaction design.…”

Section: Introductionmentioning

confidence: 99%

Mechanistic Investigations of the Iron(III)-Catalyzed Carbonyl-Olefin Metathesis Reaction

et al. 2017

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Iron(III)-catalyzed carbonyl-olefin ring-closing metathesis represents a new approach toward the assembly of molecules traditionally generated by olefin-olefin metathesis or olefination. Herein, we report detailed synthetic, spectroscopic, kinetic, and computational studies in order to determine the mechanistic features imparted by iron(III), substrate, and temperature to the catalytic cycle. These data are consistent with an iron(III)-mediated asynchronous, concerted [2+2]-cycloaddition to form an intermediate oxetane as the turnover limiting step. Fragmentation of the oxetane via Lewis acid-activation results in the formation of 5- and 6-membered unsaturated carbocycles.

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Section: Introductionmentioning

confidence: 99%

Mechanistic Investigations of the Iron(III)-Catalyzed Carbonyl-Olefin Metathesis Reaction

et al. 2017

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“…Zu erwähnen ist, dass die starken Hinweise füre ine konzertierte asynchrone Oxetan-Bildung von der Schindler-Gruppe auf Studien mit 1,3-Dicarbonylverbindungen beruhen. [7,8] [c] Ausbeuteanisoliertem Produkt (Werte in Klammern gehçren zu dem FeCl 3 -Experiment). Es erscheint wahrscheinlich, dass der Mechanismus der Oxetan-Bildung vom verwendeten Substrattyp abhängt.…”

Section: Zuschriftenunclassified

“…Demgegenüber wurde der hier präsentierte Hinweis und der Hinweis aus der Li-Gruppe mit d,eungesättigten Arylketonen gewonnen. [7,8] Schema 1. Der berichtete Einfluss des Olefin-Substitutionsmusters auf den Mechanismus der Oxetan-Bildung bekräftigt diese Hypothese zusätzlich.…”

Section: Zuschriftenunclassified

“…[3] 2012 verçffentlichte die Lambert-Gruppe eine organokatalytische Carbonyl-Olefin-Ringçffnungsmetathese. [6,7] Kurze Zeit später wurde durch die Li-Gruppe ein ähnlicher Lçsungsansatz fürden Aufbau von carbo-und heterocyclischen Alkenen beschrieben. Des Weiteren wurde eine Lewis-Säure-katalysierte intermolekulare Carbonyl-Olefin-Metathese durch FranzØn et al unter Verwendung von 20 Mol-% Tr ityltetrafluoroborat beschrieben.…”

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Brønsted‐Säure‐katalysierte Carbonyl‐Olefin‐Metathese in einer selbstorganisierten supramolekularen Wirtstruktur

Catti

Tiefenbacher

2018

Angewandte Chemie

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Die Carbonyl-Olefin-Metathese ist eine leitsungsfähige,a ber unterentwickelte Methode fürd ie Ausbildung von Kohlenstoff-Kohlenstoff-Bindungen. Bisher wurde kein Brønsted-Säure-basiertes Protokoll fürd ie katalytischeC arbonyl-Olefin-Metathese in der Literatur beschrieben. Wir präsentieren ein cokatalytisches System, das auf einer einfachen Brønsted-Säure (HCl) und einer selbstassemblierenden supramolekularen Wirtstruktur basiert. Das entwickelte System schneidet im Vergleichm it dem derzeitigen Benchmark-Katalysator fürd ie Carbonyl-Olefin-Metathese hinsichtlich Substratbreite und Ausbeute gut ab.D ie durchgeführten Kontrollversuchel iefern sehr gute Hinweise,d ass die Reaktion innerhalb der Kavitätd es supramolekularen Wirts abläuft. Eine mechanistische Studie deutet auf einen schrittweisen Reaktionsmechanismus hin.

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“…16 PACs represent important structural motifs in materials science, natural product synthesis, and asymmetric catalysis. The optimized conditions for iron(III)-catalyzed carbonyl-olefin metathesis proved efficient for a wide range of functionalized biaryl ketones 93 to result in the formation of the desired metathesis products 94 in high yields (Scheme 15).…”

Section: Lewis Acid-catalyzed Carbonyl-olefin Metathesismentioning

confidence: 99%

Lewis Acid Catalyzed Carbonyl–Olefin Metathesis

Ludwig

Schindler

2017

Synlett

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The formation of carbon-carbon bonds is of fundamental importance in the field of synthetic organic chemistry and is therefore invaluable for the synthesis of many important biologically active molecules, including current pharmaceuticals and complex natural products. The development of new, sustainable, efficient, and selective catalytic procedures for carbon-carbon bond formation, therefore, represents a key research goal in synthetic chemistry.The metathesis reaction between two alkenes 1 and 2 (Scheme 1) to result in the formation of two distinct olefinic products 3 and 4 is among the most powerful catalytic carbon-carbon bond-forming reactions known and has led to profound synthetic developments in the petroleum, materials, agricultural, and pharmaceutical industries.1 The corresponding carbonyl-olefin metathesis reaction between an olefin 5 and a carbonyl 6 (Scheme 1) similarly enables the direct construction of carbon-carbon bonds, resulting in the formation of olefin 7 and carbonyl 8, [2][3][4] and has the potential to have an analogous impact on synthetic strategy (Scheme 1). 5 However, compared to the olefin-olefin metathesis reaction, currently available procedures for carbonyl-olefin metathesis are significantly less advanced. This Synpacts article is focused on our work in the area of Lewis acid mediated and Lewis acid catalyzed carbonylolefin metathesis reactions.

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Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl–Olefin Metathesis

Cited by 124 publications

References 60 publications

Mechanistic Investigations of the Iron(III)-Catalyzed Carbonyl-Olefin Metathesis Reaction

Mechanistic Investigations of the Iron(III)-Catalyzed Carbonyl-Olefin Metathesis Reaction

Brønsted‐Säure‐katalysierte Carbonyl‐Olefin‐Metathese in einer selbstorganisierten supramolekularen Wirtstruktur

Lewis Acid Catalyzed Carbonyl–Olefin Metathesis

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