Palladium(0)-catalyzed Amino-Heck Reaction of γ,δ-Unsaturated Ketone N,N,N-Trimethylhydrazonium Salts

Narasaka, Koichi; Kitamura, Masaya; Yanagisawa, Hideyuki; Yamane, Masaaki

doi:10.3987/com-04-10280

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Cited by 15 publications

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Cyclization of Vinyl and Aryl Azides into Pyrroles, Indoles, Carbazoles, and Related Fused Pyrroles

Berkowitz

McCombie

2017

Organic Reactions

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This chapter reviews in detail those reactions that form of a new pyrrole ring from vinyl, aryl, and heteroaryl azides via formal C–H insertion processes under thermal, photochemical, and metal‐catalyzed conditions. These reactions proceed via the intermediacy of vinyl or aryl nitrenes (or their metallonitrene equivalents) and generate a wide variety of pyrroles, indoles, carbazoles, and related systems. Methods for the synthesis of the starting azides are summarized, and a comprehensive survey of the cyclization processes is provided.

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Cyclization of Vinyl and Aryl Azides into Pyrroles, Indoles, Carbazoles, and Related Fused Pyrroles

Berkowitz

McCombie

2017

Organic Reactions

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Highly Efficient Narasaka–Heck Cyclizations Mediated by P(3,5‐(CF₃)₂C₆H₃)₃: Facile Access to N‐Heterobicyclic Scaffolds

Faulkner

Bower

2012

Angewandte Chemie

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Direkt zu N‐Heterobicyclen: Palladiumkatalysierte Cyclisierungen von Oximestern mit cyclischen Alkenen eignen sich als allgemeine Route zu Perhydroindolen und verwandten Molekülgerüsten. Für die entscheidende C(sp3)‐N‐Verknüpfung ist der Ligand P(3,5‐(CF3)2C6H3)3 unverzichtbar. Mithilfe dieser Methode können Substrate mit unterschiedlichen sterischen und elektronischen Eigenschaften effizienter cyclisiert werden.

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Highly Efficient Narasaka–Heck Cyclizations Mediated by P(3,5‐(CF₃)₂C₆H₃)₃: Facile Access to N‐Heterobicyclic Scaffolds

Faulkner¹,

Bower²

2012

Angew Chem Int Ed

119

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N‐heterobicyclic scaffolds: Highly efficient palladium‐catalyzed cyclizations of oxime esters with cyclic alkenes were used as a general entry to perhydroindole and related scaffolds. The chemistry is reliant upon the use of P(3,5‐(CF3)2C6H3)3 for the key C(sp3)N bond‐forming process and this facilitates cyclizations with enhanced levels of efficiency across a range of sterically and electronically distinct substrates.

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Palladium(0)-catalyzed Amino-Heck Reaction of γ,δ-Unsaturated Ketone N,N,N-Trimethylhydrazonium Salts

Cited by 15 publications

References 16 publications

Cyclization of Vinyl and Aryl Azides into Pyrroles, Indoles, Carbazoles, and Related Fused Pyrroles

Cyclization of Vinyl and Aryl Azides into Pyrroles, Indoles, Carbazoles, and Related Fused Pyrroles

Highly Efficient Narasaka–Heck Cyclizations Mediated by P(3,5‐(CF₃)₂C₆H₃)₃: Facile Access to N‐Heterobicyclic Scaffolds

Highly Efficient Narasaka–Heck Cyclizations Mediated by P(3,5‐(CF₃)₂C₆H₃)₃: Facile Access to N‐Heterobicyclic Scaffolds

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Palladium(0)-catalyzed Amino-Heck Reaction of γ,δ-Unsaturated Ketone N,N,N-Trimethylhydrazonium Salts

Cited by 15 publications

References 16 publications

Cyclization of Vinyl and Aryl Azides into Pyrroles, Indoles, Carbazoles, and Related Fused Pyrroles

Cyclization of Vinyl and Aryl Azides into Pyrroles, Indoles, Carbazoles, and Related Fused Pyrroles

Highly Efficient Narasaka–Heck Cyclizations Mediated by P(3,5‐(CF3)2C6H3)3: Facile Access to N‐Heterobicyclic Scaffolds

Highly Efficient Narasaka–Heck Cyclizations Mediated by P(3,5‐(CF3)2C6H3)3: Facile Access to N‐Heterobicyclic Scaffolds

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Highly Efficient Narasaka–Heck Cyclizations Mediated by P(3,5‐(CF₃)₂C₆H₃)₃: Facile Access to N‐Heterobicyclic Scaffolds

Highly Efficient Narasaka–Heck Cyclizations Mediated by P(3,5‐(CF₃)₂C₆H₃)₃: Facile Access to N‐Heterobicyclic Scaffolds