Regioselective Synthesis of 5-Metalated 2-Pyrones by Intramolecular Oxymetalation of Carbonyl-ene-yne Compounds Using Indium Trihalide

Yata, Tetsuji; Kita, Yoshiyuki; Nishimoto, Yoshihiro; Yasuda, Makoto

doi:10.1021/acs.joc.9b02186

Cited by 26 publications

(15 citation statements)

References 52 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In 2019, the group of Nishimoto reported a process for the oxyindation of carbonyl‐ene‐yne compounds to give metalated 2‐pyrones, which could be further transferred into highly substituted 2‐pyrones by simple cross‐coupling [79] . Some of the obtained tetrasubstituted 2‐pyrones showed bright emission in the solid state.…”

Section: Aiegen Diversification By Metal‐free Proceduresmentioning

confidence: 99%

Innovative Synthetic Procedures for Luminogens Showing Aggregation‐Induced Emission

et al. 2021

View full text Add to dashboard Cite

As a consequence of their intrinsic advantageous properties, luminogens that show aggregation‐induced emission (AIEgens) have received increasing global interest for a wide range of applications. Whereas general synthetic methods towards AIEgens largely rely on tedious procedures and limited reaction types, various innovative synthetic methods have now emerged as complementary, and even alternative, strategies. In this Review, we systematically highlight advancements made in metal‐catalyzed functionalization and metal‐free‐promoted pathways for the construction of AIEgens over the past five years, and briefly illustrate new perspectives in this area. The development of innovative synthetic procedures will enable the facile synthesis of AIEgens with great structural diversity for multifunctional applications.

show abstract

Section: Aiegen Diversification By Metal‐free Proceduresmentioning

confidence: 99%

Innovative Synthetic Procedures for Luminogens Showing Aggregation‐Induced Emission

et al. 2021

View full text Add to dashboard Cite

show abstract

“…[50] Likewise, oxyindation with indium trihalides furnished 5-metalated pyrones that enabled easy access to various multi functionalized 2-pyrones 135 by subsequent halogenations or cross-coupling reactions. [51] In contrast to the first two reports, no competitive 5-exo-dig cyclization was observed in the boron-and indium-mediated protocols which can be rationalized by selective formation of intermediate 134.…”

Section: Transition-metal-free Synthesismentioning

confidence: 79%

2‐Pyrone – A Privileged Heterocycle and Widespread Motif in Nature

et al. 2021

View full text Add to dashboard Cite

In memory of Klaus HafnerThe 2-pyrone moiety can be found in a large number of natural products with a wide range of biological activities, including antibiotic, antifungal, cytotoxic, neurotoxic, phytotoxic, antiinflammatory and cardiotonic effects. With its heterocyclic structure encompassing the chemical nature of conjugated dienes, lactones, Michael acceptors and arenes, it can undergo a great variety of transformations such as cycloadditions, ringopening reactions, cross-couplings and lactamizations. Thus, 2-pyrones represent valuable synthetic precursors and worthwhile targets in organic, polymer, and medical chemistry. Owing to its exquisite chemical and physical properties, the synthesis and further transformations of 2-pyrones have attracted considerable attention over the past decade, showcasing transition metal and metal free strategies and using readily available starting materials, notably those stemming from renewable resources.

show abstract

“…2019 veröffentlichte die Gruppe von Nishimoto ein Verfahren zur Oxyindierung von Carbonyl‐En‐In‐Verbindungen, um metallierte 2‐Pyrone zu erhalten, die durch eine einfache Kreuzkupplung weiter zu hochsubstituierten 2‐Pyronen umgewandelt werden konnten [79] . Einige der hergestellten tetrasubstituierten 2‐Pyrone zeigten im festen Zustand eine helle Emission.…”

Section: Erweiterung Der Vielfalt Von Aiegenen Mit Metallfreien Verfahrenunclassified

Innovative Verfahren zur Synthese von Luminogenen mit aggregationsinduzierter Emission

Yan

Wang

et al. 2021

Angewandte Chemie

View full text Add to dashboard Cite

Wegen ihrer Vorteile haben Luminogene mit aggregationsinduzierter Emission (AIEgene) in einer Reihe von Anwendungsbereichen weltweit wachsendes Interesse auf sich gezogen. Während allgemeine Verfahren zur Synthese von AIEgenen im Wesentlichen auf schwierigen Abläufen und eingeschränkten Reaktionstypen beruhen, haben sich in diesem Zusammenhang verschiedene innovative Syntheseverfahren als ergänzende oder sogar alternative Strategien herausgebildet. In diesem Aufsatz zeigen wir systematisch die neuesten Fortschritte bei der metallkatalysierten Funktionalisierung und den nicht metallgeförderten Wegen zum Aufbau von AIEgenen der letzten fünf Jahre auf und erläutern kurz neue Perspektiven auf diesem Gebiet. Die Entwicklung innovativer Verfahren ist vielversprechend für die zukünftige Herstellung von AIEgenen, wobei eine einfache Synthese, eine große Strukturvielfalt und multifunktionale Anwendungen ermöglicht werden sollen.

show abstract

Regioselective Synthesis of 5-Metalated 2-Pyrones by Intramolecular Oxymetalation of Carbonyl-ene-yne Compounds Using Indium Trihalide

Cited by 26 publications

References 52 publications

Innovative Synthetic Procedures for Luminogens Showing Aggregation‐Induced Emission

Innovative Synthetic Procedures for Luminogens Showing Aggregation‐Induced Emission

2‐Pyrone – A Privileged Heterocycle and Widespread Motif in Nature

Innovative Verfahren zur Synthese von Luminogenen mit aggregationsinduzierter Emission

Contact Info

Product

Resources

About