Ruthenium Complex-Catalyzed Direct Ortho Arylation and Alkenylation of 2-Arylpyridines with Organic Halides

Ôi, Shuichi; Fukita, Susumu; Hirata, Naomi; Watanuki, Noboru; Miyano, Sotaro; Inoue, Yoshio

doi:10.1021/ol016257z

Cited by 338 publications

(144 citation statements)

References 30 publications

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“…Aryl Iodides and Bromides A catalytic system consisting of [{RuCl 2 (h 6 -C 6 H 6 )} 2 ] and PPh 3 was elegantly exploited by Oi, Inoue et al for the direct arylation of 2-aryl pyridine derivatives with aryl bromides as the electrophiles (Scheme 127). [223] The same procedure proved applicable to the directed arylation of substituted ketimines, imidazolines, and oxazolines as pronucleophilic starting materials. [224] Transformations of the latter substrates should prove valuable, since 2-oxazolinyl substituents can be easily converted into a variety of valuable functionalities.…”

Section: Ruthenium-catalyzed Direct Arylationmentioning

confidence: 95%

Transition‐Metal‐Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage

2009

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The area of transition-metal-catalyzed direct arylation through cleavage of C-H bonds has undergone rapid development in recent years, and is becoming an increasingly viable alternative to traditional cross-coupling reactions with organometallic reagents. In particular, palladium and ruthenium catalysts have been described that enable the direct arylation of (hetero)arenes with challenging coupling partners--including electrophilic aryl chlorides and tosylates as well as simple arenes in cross-dehydrogenative arylations. Furthermore, less expensive copper, iron, and nickel complexes were recently shown to be effective for economically attractive direct arylations.

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Section: Ruthenium-catalyzed Direct Arylationmentioning

confidence: 95%

Transition‐Metal‐Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage

2009

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“…Die ausgezeichnete katalytische Aktivität ermöglichte ebenfalls effiziente Arylierungen von Pyridinderivaten [25] als Pronucleophilen unter Verwendung von Aryltosylaten. Interessanterweise konnte die Selektivität der C-H-Bindungsaktivierung durch die Wahl des Elektrophils gesteuert werden (Tabelle 3).…”

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Katalytische Arylierungen über C‐H‐Bindungsaktivierung mit Aryltosylaten

2006

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“…Screening literature conditions, we identified a ruthenium (II) catalyzed method which could be modified in a way that it fulfilled our requirements. 42,43 There, NMP was used as solvent at 120 °C in combination with…”

Section: Methodsmentioning

confidence: 99%

Exploiting the C-H bond in metal catalyzed C-C bond forming reactions

Schnürch¹

2015

Arkivoc

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This account summarizes our work in the field of direct C-H bond functionalization. We have explored methods in the area of directing group assisted C(sp 2 )-H and C(sp 3 )-H activation and investigated arylation as well as deuteration reactions. In these transformations either ruthenium or palladium catalysts were applied. In case of C(sp 2 )-H activation, we developed a protocol for the synthesis of ortho arylated anilines and disclosed the first method for a direct arylation in a continuous flow reactor. Additionally, we applied a direct arylation in the synthesis of compounds which can accelerate cell differentiation. In the field of C(sp 3 )-H activation we developed a protocol for the selective mono-arylation of piperidine and three different arylation protocols for acyclic amines employing either aryl chlorides, aryl bromides, aryl iodides, or arylboronic acid esters as the aryl donor.

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Ruthenium Complex-Catalyzed Direct Ortho Arylation and Alkenylation of 2-Arylpyridines with Organic Halides

Abstract: [reaction: see text] The ortho position of the aromatic ring of pyridyl group-substituted aromatic compounds is directly arylated or alkenylated with organic halides in the presence of a catalytic amount of a ruthenium(II)-phosphine complex.

Cited by 338 publications

References 30 publications

Transition‐Metal‐Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage

Transition‐Metal‐Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage

Katalytische Arylierungen über C‐H‐Bindungsaktivierung mit Aryltosylaten

Exploiting the C-H bond in metal catalyzed C-C bond forming reactions

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