Formal Synthesis of Nitidine and NK109 via Palladium-Catalyzed Domino Direct Arylation/<i>N</i>-Arylation of Aryl Triflates

Blanchot, Mathieu; Candito, David A.; Larnaud, Florent; Lautens, Mark

doi:10.1021/ol200174g

Cited by 134 publications

(47 citation statements)

References 44 publications

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“…In 2011, Lautens and coworkers achieved a formal synthesis of nitidine and NK 109 through a tandem direct arylation/N-arylation strategy (Scheme 16.33) [67]. To this end, aryl triflate 152 and imine 153 were coupled together by the action of a palladium catalyst and norbornene to give coupling product 155.…”

Section: Nitidine and Nk 109 (Catellani-type C-h Arylation/n-arylation)mentioning

confidence: 99%

Synthesis of Natural Products and Pharmaceuticals via Catalytic CH Functionalization

Yamaguchi¹,

Amaike²,

Itami³

2016

Transition Metal‐Catalyzed Heterocycle Synthesis via CH Activation

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Section: Nitidine and Nk 109 (Catellani-type C-h Arylation/n-arylation)mentioning

confidence: 99%

Synthesis of Natural Products and Pharmaceuticals via Catalytic CH Functionalization

Yamaguchi¹,

Amaike²,

Itami³

2016

Transition Metal‐Catalyzed Heterocycle Synthesis via CH Activation

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“…6 Several intramolecular N-arylation of N,N-disubstituted amindines have been reported recently. 11 Nontheless, these methods have certain limitations such as strongly acidic or basic conditions, high temperature, using stoichiometric or catalytic amounts of transition metals, or the preparation of activated intermediates. A simple and general metal-free N-arylation procedure to directly generate N-arylated amidines from amidines and N,N-disubstituted amidines, or their salts under mild reaction conditions should be very attractive, since it offers efficient access to a variety of such compounds.…”

Section: Graphical Abstractmentioning

confidence: 99%

Facile N-arylation of amidines and N,N-disubstituted amidines

Yao

2015

Tetrahedron Letters

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“…The use of aryl triflates has been reported recently, allowing an interesting extension of the substrate scope [12].…”

Section: Oxidative Addition and Carbopalladationmentioning

confidence: 99%

“…Along with N-silylaldimines, unsubstituted ketimines could be conveniently used in this procedure. Remarkably, silylimine 79 could react smoothly with aryl triflate 80 to deliver benzo[c]phenanthridine 81, a key precursor of natural phenanthridinium alkaloid nitidine [12].…”

Section: Aromatic Arylations Coupled With N-aryl Couplingsmentioning

confidence: 99%

Bibliographical Background: The Ortho Effect in The Catellani Reaction

Larraufie

2013

Development of New Radical Cascades and Multi-Component Reactions

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Pallado-catalyzed sequential reactions involving direct C-H bond activations have emerged as powerful tools for rapid access to complex polycyclic scaffolds, starting from simple precursors [1][2][3]. In this context, Professor Marta Catellani has pioneered in the mid 1980s the utilization of norbornene in cooperation with palladium to achieve sequential C-halide and C-H activations via the formation of a five-membered alkylaromatic palladacycle. In 1985, she published the synthesis of dihydrophenanthrene 1 by coupling of two molecules of bromobenzene and one of norbornene, through the proposed formation of palladacycle 2 ( Fig. 7.1) [4].Since then, numerous applications of palladium/norbornene-mediated domino processes have been reported, allowing the synthesis of various polycyclic frameworks and the construction of up to three carbon-carbon bonds in a single reaction [5][6][7]. The catalytic cycle of the Catellani reaction, involving multiple oxidation state of palladium (0, II and potentially IV), will be presented first. Several examples of the synthetic scope of this methodology will follow, with a special focus on the sequences involving aryl-aryl coupling. Palladacycle FormationThe Catellani reaction is based on the formation of palladium(II) metallacycles 7 and their ability to react with electrophiles such as aryl and alkyl halides. The palladacycle is generated from palladium(0) complex 3, aryl halide 4 and norbornene. Generally, Pd(0) catalysts are not air stable, so the in situ generation of Pd(0) species by reaction of palladium(II) salts with phosphines [8,9]

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Formal Synthesis of Nitidine and NK109 via Palladium-Catalyzed Domino Direct Arylation/N-Arylation of Aryl Triflates

Abstract: The use of aryl triflates as reaction partners in a palladium-catalyzed domino direct arylation/N-arylation provides a great advantage due to the availability of starting materials. Furthermore, it allows expedient access to biologically interesting benzo[c]phenanthridine alkaloids.

Cited by 134 publications

References 44 publications

Synthesis of Natural Products and Pharmaceuticals via Catalytic CH Functionalization

Synthesis of Natural Products and Pharmaceuticals via Catalytic CH Functionalization

Facile N-arylation of amidines and N,N-disubstituted amidines

Bibliographical Background: The Ortho Effect in The Catellani Reaction

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