Palladium-catalyzed iminocarbonylative cross-coupling reaction between haloarenes, t-BuNC, and 9-alkyl-9-BBN derivatives. Synthesis of alkyl aryl ketones

Ishiyama, Tatsuo; Oh-e, Takayuki; Miyaura, Norio; Suzuki, Akira

doi:10.1016/s0040-4039(00)60111-9

Cited by 48 publications

(16 citation statements)

References 7 publications

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“…[12] One of the few three-component imine syntheses consists of the catalytic cross-coupling of aryl halides with organometallic reagents in the presence of toxic and malodorous isonitriles (VI). [13] We herein present a highly modular entry to the azomethine moiety, involving the decarboxylative coupling of aryl halides and a-iminocarboxylates, generated in situ from potassium a-oxocarboxylates and primary amines (Scheme 2).…”

mentioning

confidence: 99%

Synthesis of Azomethines from α‐Oxocarboxylates, Amines and Aryl Bromides via One‐Pot Three‐Component Decarboxylative Coupling

2011

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mentioning

confidence: 99%

Synthesis of Azomethines from α‐Oxocarboxylates, Amines and Aryl Bromides via One‐Pot Three‐Component Decarboxylative Coupling

2011

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“…(69)]. [103] Strong bases and polar solvents lower the yield as do electron-withdrawing substituents on the iodoarene. The reaction is sensitive to the stoichiometry of the isonitrile and the 9-alkyl-9-BBN derivative; a 1:1 ratio being optimal.…”

Section: Condensations Affording Iminesmentioning

confidence: 99%

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

et al. 2014

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Isonitriles are delicately poised chemical entities capable of being coaxed to react as nucleophiles or electrophiles. Directing this tunable reactivity with metal and non-metal catalysts provides rapid access to a large array of complex nitrogenous structures ideally functionalized for medicinal applications. Isonitrile insertion into transition metal complexes has featured in numerous synthetic and mechanistic studies, leading to rapid deployment of isonitriles in numerous catalytic processes, including multicomponent reactions (MCR). Covering the literature from 1990–2014, the present review collates reaction types to highlight reactivity trends and allow catalyst comparison.

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“…[45] Die palladiumkatalysierte Insertion von Isocyaniden in S-S-Bindungen wurde ausführlich von Kurosawa et al untersucht, die zeigten, dass die Isocyanidinsertion in Pd-S-Bindungen reversibel ist. [47] Die bençtigten 9-Alkyl-BBN-Derivate (119) wurden in situ hergestellt und direkt eingesetzt. [47] Die bençtigten 9-Alkyl-BBN-Derivate (119) wurden in situ hergestellt und direkt eingesetzt.…”

Section: Verschiedene Palladiumkatalysierte Isocyanidinsertionenunclassified

Palladiumkatalysierte migratorische Insertion von Isocyaniden: eine neue Methode für die Kreuzkupplungschemie

et al. 2013

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Seit der Entdeckung der Ugi‐Reaktion und ähnlicher Isocyanid‐ basierter Mehrkomponentenreaktionen sind Isocyanide wichtige Bausteine für die organische Synthese. In den letzten zehn Jahren fanden Isocyanide als vielseitige C1‐Bausteine in der Palladiumkatalyse eine neue Anwendung. Palladiumkatalysierte Reaktionen, die unter Isocyanidinsertion ablaufen, bieten ein enormes Potenzial für die Synthese stickstoffhaltiger Feinchemikalien. In diesem Kurzaufsatz werden alle erzielten Erfolge auf diesem neu entstehenden Gebiet diskutiert.

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Palladium-catalyzed iminocarbonylative cross-coupling reaction between haloarenes, t-BuNC, and 9-alkyl-9-BBN derivatives. Synthesis of alkyl aryl ketones

Cited by 48 publications

References 7 publications

Synthesis of Azomethines from α‐Oxocarboxylates, Amines and Aryl Bromides via One‐Pot Three‐Component Decarboxylative Coupling

Synthesis of Azomethines from α‐Oxocarboxylates, Amines and Aryl Bromides via One‐Pot Three‐Component Decarboxylative Coupling

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

Palladiumkatalysierte migratorische Insertion von Isocyaniden: eine neue Methode für die Kreuzkupplungschemie

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