Palladium‐Catalyzed Regioselective Mono‐ and Diarylation Reactions of 2‐Phenylphenols and Naphthols with Aryl Halides

Satoh, Tetsuya; Kawamura, Yuichiro; Miura, Masahiro; Nomura, Masakatsu

doi:10.1002/anie.199717401

Cited by 569 publications

(222 citation statements)

References 26 publications

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“…Originally reported by Palucki and Buchwald (30), Hamann and Hartwig (31), and Miura and coworkers (32), the palladiumcatalyzed α-arylation of enolates has recently emerged as a powerful new reaction in synthetic organic chemistry (33)(34)(35). Key to its success has been the design of appropriate ligands for palladium that have precisely engineered steric and electronic properties to enable the various steps in the catalytic cycle to proceed with maximum efficiency (36)(37)(38)(39).…”

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confidence: 99%

Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones

Donohoe

Pilgrim

Jones

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

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The utilization of sequential palladium-catalyzed α-arylation and cyclization reactions provides a general approach to an array of isoquinolines and their corresponding N-oxides. This methodology allows the convergent combination of readily available precursors in a regioselective manner and in excellent overall yields. This powerful route to polysubstituted isoquinolines, which is not limited to electron rich moieties, also allows rapid access to analogues of biologically active compounds.T he isoquinoline motif and its derivatives form the cores of numerous natural products (1, 2), are the central components of a number of pharmaceutical agents (3-5), and can provide the scaffold for chiral ligands (6, 7) and valuable organic materials (8). However, traditional isoquinoline syntheses such as the Bischler-Napieralski (9, 10), 12), and Pomeranz-Fritsch reactions (13-15) all centre around the lynchpin of electrophilic aromatic substitution and are thus often limited to electron-rich carbocycles (Scheme 1A). It is also imperative to develop routes to highly-substituted isoquinolines to fully explore this chemical space, for example, for potential pharmaceutical targets. While recent synthetic efforts have greatly expanded the diversity of isoquinoline motifs available (16-29), new routes to isoquinolines are still highly desirable, particularly ones with the ability to directly access the isoquinoline moiety in a range of oxidation levels and which do not require highly-specialized starting materials.Originally reported by Palucki and Buchwald (30), Hamann and Hartwig (31), and Miura and coworkers (32), the palladiumcatalyzed α-arylation of enolates has recently emerged as a powerful new reaction in synthetic organic chemistry (33-35). Key to its success has been the design of appropriate ligands for palladium that have precisely engineered steric and electronic properties to enable the various steps in the catalytic cycle to proceed with maximum efficiency (36-39). The reaction's utility has also been greatly enhanced by the development of robust preformed palladium catalysts. Properties such as air stability and very high reactivity in a range of systems have greatly expanded the potential uses of these catalysts (40-43). However, the α-arylation reaction has seen limited use in the de novo construction of aromatic compounds (44-51) and is still greatly underused in this regard, especially because the bond forming abilities provided by this powerful reaction can greatly simplify the design of routes to heavily-substituted aromatic compounds. Hence, we decided to explore the scope of this new catalytic method in the synthesis of important heteroaromatic ring systems, beginning our investigations with the isoquinoline nucleus. ResultsIn our disconnection approach we envisaged that key pseudo-1,5-dicarbonyl intermediates 3 could be accessed via the palladiumcatalyzed α-arylation of ketones 1 with aryl halides 2 possessing a protected aldehyde or ketone in the ortho-position (52). Subsequent treatment of these inter...

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confidence: 99%

Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones

Donohoe

Pilgrim

Jones

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

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“…In summary, we have found the use of H 8 -BINAP as a ligand, compared with carbene ligand 1, improved reaction conversions in an enantioselective intramolecular a-arylation [16][17][18][19][20] …”

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Asymmetric Construction of Quaternary Carbon Stereocenter by Pd-Catalyzed Intramolecular .ALPHA.-Arylation

Arao

Kondo

Aoyama

2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…At the same time, trying the Miura, 18 Buchwald 19 and Hartwig 20 palladium-catalyzed conditions, such as Pd 2 (dba) 3 (2.5 mol%), K 3 PO 4 as base in toluene at 70 ºC under Ar atmosphere, the same aromatization process was observed. These unexpected results prompted us to develop reaction conditions to the general synthesis of 1-hydroxy-2-naphthoates 1 from the corresponding 2-(methoxycarbonyl)-α-tetralones 5.…”

Section: A C C E P T E D Accepted Manuscriptmentioning

confidence: 68%

Two-dimensional Cu deposition on Pt(100) and stepped surfaces of platinum single crystals

Molodkina

Ehrenburg

Данилов

et al. 2016

Electrochimica Acta

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Palladium‐Catalyzed Regioselective Mono‐ and Diarylation Reactions of 2‐Phenylphenols and Naphthols with Aryl Halides

Cited by 569 publications

References 26 publications

Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones

Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones

Asymmetric Construction of Quaternary Carbon Stereocenter by Pd-Catalyzed Intramolecular .ALPHA.-Arylation

Two-dimensional Cu deposition on Pt(100) and stepped surfaces of platinum single crystals

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