Ketene Three‐Component Reaction: A Metal‐Free Multicomponent Approach to Stereodefined Captodative Olefins

Basso, Andrea; Banfi, Luca; Garbarino, Silvia; Riva, Renata

doi:10.1002/ange.201209399

Angewandte Chemie

2013

DOI: 10.1002/ange.201209399

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Ketene Three‐Component Reaction: A Metal‐Free Multicomponent Approach to Stereodefined Captodative Olefins

Andrea Basso

Luca Banfi

Silvia Garbarino

et al.

Abstract: Drei im Rampenlicht: Lichteinstrahlung vermittelt eine allgemeine Dreikomponentenreaktion zwischen Diazoketonen, Carbonsäuren und Isocyaniden. Die hoch funktionalisierten captodativen Olefinprodukte dieser Reaktion sind vielseitige Synthone für die organische Synthese.

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Cited by 9 publications

(1 citation statement)

References 21 publications

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“…44,45 Ketenes have been used for the synthesis of four membered rings via [2 + 2] cycloadditions and, more recently, in multicomponent reactions. 46 A recent approach makes use of the photoinduced conversion of acyl silanes into the corresponding siloxycarbenes (Scheme 8b).…”

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Carbon–Carbon Bond Forming Reactions via Photogenerated Intermediates

2016

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The present review offers an overview of the current approaches for the photochemical and photocatalytic generation of reactive intermediates and their application in the formation of carbon-carbon bonds. Valuable synthetic targets are accessible, including arylation processes, formation of both carbo- and heterocycles, alpha- and beta-functionalization of carbonyls, and addition reactions onto double and triple bonds. According to the recent advancements in the field of visible/solar light catalysis, a significant part of the literature reported herein involves radical ions and radicals as key intermediates, with particular attention to the most recent examples. Synthetic application of carbenes, biradicals/radical pairs and carbocations have been also reported.

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Carbon–Carbon Bond Forming Reactions via Photogenerated Intermediates

2016

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Photoinduzierte Mehrkomponentenreaktionen

et al. 2016

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Die Kombination von Mehrkomponentenansätzen mit lichtgetriebenen Prozessen erschließt neue Bereiche auf dem Gebiet der organischen Synthesechemie, deren Bedarf an nachhaltigen und atom‐ sowie energieeffizienten Reaktionen immer dringlicher wird. Photoinduzierte Mehrkomponentenreaktionen befinden sich noch immer in einem frühen Stadium, für die nahe Zukunft ist jedoch mit deutlichen Fortschritten zu rechnen.

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Visible‐Light‐Induced Passerini Multicomponent Polymerization

et al. 2019

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Herein, we introduce an additive-free visible-lightinduced Passerini multicomponent polymerization (MCP) for the generation of high molar mass chains.Inplace of classical aldehydes (or ketones), highly reactive,insitu photogenerated thioaldehydes are exploited along with isocyanides and carboxylic acids.P rone to side reactions,t he thioaldehyde moieties create ac omplex reaction environment which can be tamed by optimizing the synthetic conditions utilizing stochastic reaction path analysis,h ighlighting the potential of semibatch procedures.O nce the complex MCP environment is understood, step-growth polymers can be synthesized under mild reaction conditions which-after aM umm rearrangement-result in the incorporation of thioester moieties directly into the polymer backbone,leading to soft matter materials that can be degraded by straightforwarda minolysis or chain expanded by thiirane insertion.

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Ketene Three‐Component Reaction: A Metal‐Free Multicomponent Approach to Stereodefined Captodative Olefins

Abstract: Drei im Rampenlicht: Lichteinstrahlung vermittelt eine allgemeine Dreikomponentenreaktion zwischen Diazoketonen, Carbonsäuren und Isocyaniden. Die hoch funktionalisierten captodativen Olefinprodukte dieser Reaktion sind vielseitige Synthone für die organische Synthese.

Cited by 9 publications

References 21 publications

Carbon–Carbon Bond Forming Reactions via Photogenerated Intermediates

Carbon–Carbon Bond Forming Reactions via Photogenerated Intermediates

Photoinduzierte Mehrkomponentenreaktionen

Visible‐Light‐Induced Passerini Multicomponent Polymerization

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