A reinvestigation of known bromination reactions of quinoline

Butler, Jerry L.; Gordon, Marshall

doi:10.1002/jhet.5570120539

Cited by 28 publications

(12 citation statements)

References 7 publications

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“…[31] Interestingly, bromination of nonchelated naphthyl derivatives [OsCl(1-naphthyl)(CO)(PPh 3 ) 2 ] under the same reaction conditions resulted in cleavage of the Os-naphthyl bond. This result highlights again the key role played by chelation to stabilize the M À C s bond.…”

Section: Regioselective Electrophilic Substitution Of Heterocyclic Pomentioning

confidence: 98%

Organic Transformations on σ‐Aryl Organometallic Complexes

et al. 2007

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This work reviews recent developments in the field of organic transformations on sigma-aryl organometallic complexes. The general notion that M--C sigma bonds are kinetically labile, highly reactive, and incompatible with typical reaction conditions met in organic synthesis has limited the use of these synthetic strategies thus far. However, organic transformations on metal-bound sigma-aryl fragments are being used more and more by chemists in both industry and academia. In this Review, emphasis is put on the synthetic methods applied in this field up to now. The simplicity and generally good yields of these methods are very attractive for the construction of functionalized organometallic building blocks that are potentially useful as photochemical molecular devices, biosensors and -conjugates, or molecular switches. Thus, this Review has been tailored for a broader audience with the aim of encouraging the application of these strategies.

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Section: Regioselective Electrophilic Substitution Of Heterocyclic Pomentioning

confidence: 98%

Organic Transformations on σ‐Aryl Organometallic Complexes

et al. 2007

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“…The hydrosilylation reactions with the platina-b-diketones 1 and 3 proceeded noticeably faster than those with the reference catalysts 4 and 5. Due to its symmetry, the hydrosilylation of hex-3-yne yielded one main product only (11,Scheme 2). The 3 J C,H coupling constant of 10.5 Hz gave proof for the formation of the (E) isomer manifesting a syn addition of the hydrosilane.…”

Section: Hydrosilylation Of Hexynesmentioning

confidence: 99%

“…Hexachloroplatinic acid was available from m&k GmbH (47.4% Pt). The platina-b-diketones [Pt 2 {(COMe) 2 H} 2 (l-Cl) 2 ] (1) [9], [PPh 4 ][Pt{(COMe) 2 H}Cl 2 ] (2) and [Pt{(COMe) 2 }(acac)] (3) [10] as well as 8-bromoquinoline [11] and bis (8-quinolyl)methylsilane (22) [12] were prepared according to known procedures. All other substrates were commercially available and used as received.…”

Section: General Proceduresmentioning

confidence: 99%

Platina-β-diketones as catalysts for hydrosilylation and their reactivity towards hydrosilanes

Schwieger

Herzog

Wagner

et al. 2009

Journal of Organometallic Chemistry

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“…Die selektive und milde Bromierung des Chinolylliganden unter diesen Bedingungen ist bemerkenswert, denn das freie Chinolin kann auf klassische Weise nur unter drastischen Reaktionsbedingungen bromiert werden, wobei ein Produktgemisch entsteht 31. Interessanterweise führt die Bromierung der nicht‐chelatisierten Naphthylderivate vom Typ [OsCl(1‐Naphthyl)(CO)(PPh 3 ) 2 ] unter den selben Reaktionsbedingungen zu einer Spaltung der Os‐Naphthyl‐Bindung.…”

Section: Regioselektive Elektrophile Substitution Von Heterocyclisunclassified

Organische Umsetzungen an metallorganischen σ‐Aryl‐Komplexen

et al. 2007

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Dieser Aufsatz gibt einen Überblick über neue Entwicklungen auf dem Gebiet der metallvermittelten organischen Umsetzungen an metallorganischen σ‐Aryl‐Komplexen. Die allgemeine Vorstellung, dass M‐C‐σ‐Bindungen kinetisch labil, hoch reaktiv und unvereinbar mit typischen Reaktionsbedingungen der organischen Synthese sind, hat die Anwendung dieser Synthesestrategien bisher eingeschränkt. Allerdings werden metallvermittelte organische Umsetzungen an metallgebundenen σ‐Aryl‐Fragmenten immer häufiger in industriellen und Laborsynthesen eingesetzt. Die Einfachheit und im Allgemeinen guten Ausbeuten dieser Methoden sind sehr attraktiv für den Aufbau funktionalisierter metallorganischer Bausteine, die als photochemische molekulare Funktionseinheiten, Biosensoren und ‐konjugate sowie molekulare Schalter genutzt werden könnten. Dieser Aufsatz richtet sich daher an eine breitere Leserschaft und soll zum Gebrauch dieser Strategien ermutigen.

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A reinvestigation of known bromination reactions of quinoline

Cited by 28 publications

References 7 publications

Organic Transformations on σ‐Aryl Organometallic Complexes

Organic Transformations on σ‐Aryl Organometallic Complexes

Platina-β-diketones as catalysts for hydrosilylation and their reactivity towards hydrosilanes

Organische Umsetzungen an metallorganischen σ‐Aryl‐Komplexen

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