Pd/C-Catalyzed Carbonylative Synthesis of 2-Aminobenzoxazinones from 2-Iodoaryl Azides and Amines

Zhang, Youcan; Yin, Zhu; Wang, Hai; Wu, Xiao‐Feng

doi:10.1021/acs.orglett.9b00966

Cited by 19 publications

(13 citation statements)

References 47 publications

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“…In light of our results and the previous literature, ,, a possible reaction pathway is proposed as well (Scheme ). Initially, palladium nitrene species A will be formed from azide- and ligand-coordinated Pd(0) with the release of one molecule of N 2 .…”

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confidence: 67%

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Pd/C-Catalyzed Carbonylative Synthesis of α-Carbonyl-α′-Amide Sulfoxonium Ylides from Azides

et al. 2020

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The synthesis of α-carbonyl-α′-amide sulfoxonium ylides by Pd/C-catalyzed carbonylative transformation of azides with α-carbonyl sulfoxonium ylides has been studied. This method offers a direct approach to produce synthetically useful α-carbonyl-α′-amide sulfoxonium ylides in high efficiency. By using readily available substrates, 39 examples of products were prepared in good yields with outstanding functional group compatibility. An example of converting the obtained ylide into the corresponding 1,3-dicarbonyl compound has been given as well.

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confidence: 67%

“…The products were isolated from the reaction mixture by column chromatography on silica gel 60, 0.063–0.2 mm, 70–230 mesh (Merck). The sulfoxonium ylides were prepared according to the literature …”

Section: General Informationmentioning

confidence: 99%

Pd/C-Catalyzed Carbonylative Synthesis of α-Carbonyl-α′-Amide Sulfoxonium Ylides from Azides

et al. 2020

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“…[42] Ther esulting compounds exhibit strong green-yellow emission as aggregates.T he suppression of the intramolecular rotation of the phenyl and phenylene rings may account for the stronger emission in solid powders. Given the ubiquity and significance of benzoxazinones in various biologically active molecules, [43] the Zou group developed the rhodium-catalyzed CÀHa ctivation of benzoic acids for reaction with dioxazolones to afford benzoxazinone derivatives 13 in yields up to 80 %( Scheme 2D). [44] Interestingly,t he benzoxazinone products were discovered to be an ovel class of AIEgens,t ogether with having ESIPT behavior.…”

Section: Rh-catalyzed Construction Of Aiegensmentioning

confidence: 99%

Innovative Synthetic Procedures for Luminogens Showing Aggregation‐Induced Emission

et al. 2021

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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.

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“…Angesichts der Häufigkeit und Bedeutung von Benzoxazinonen in verschiedenen biologisch aktiven Molekülen [43] entwickelte die Gruppe von Zou eine rhodiumkatalysierte C-H-Aktivierung von mit Dioxazolonen reagierenden Benzoesäuren, wodurch Benzoxazinon-Derivate 13 in Ausbeuten von bis zu 80 %e rhalten wurden (Schema 2D). [44] Interessanterweise wurde zusammen mit dem ESIPT-Verhalten entdeckt, dass die als Produkte erhaltenen Benzoxazinone eine neue Klasse von AIEgenen bilden.…”

Section: Angewandte Chemieunclassified

Innovative Verfahren zur Synthese von Luminogenen mit aggregationsinduzierter Emission

Yan

Wang

et al. 2021

Angewandte Chemie

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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.

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Pd/C-Catalyzed Carbonylative Synthesis of 2-Aminobenzoxazinones from 2-Iodoaryl Azides and Amines

Cited by 19 publications

References 47 publications

Pd/C-Catalyzed Carbonylative Synthesis of α-Carbonyl-α′-Amide Sulfoxonium Ylides from Azides

Pd/C-Catalyzed Carbonylative Synthesis of α-Carbonyl-α′-Amide Sulfoxonium Ylides from Azides

Innovative Synthetic Procedures for Luminogens Showing Aggregation‐Induced Emission

Innovative Verfahren zur Synthese von Luminogenen mit aggregationsinduzierter Emission

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