Spaltung von Palladiummetallacyclen mit Säure: ein Sensor zum Studium der Cyclometallierung

Cámpora, Juan; López, Jörge A.; Valerga, Pedro; Spillner, Edzard; Carmona, Ernesto

doi:10.1002/(sici)1521-3757(19990115)111:1/2<199::aid-ange199>3.0.co;2-w

Angewandte Chemie

1999

DOI: 10.1002/(sici)1521-3757(19990115)111:1/2<199::aid-ange199>3.0.co;2-w

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Spaltung von Palladiummetallacyclen mit Säure: ein Sensor zum Studium der Cyclometallierung

Juan Cámpora

Jörge A. López

Pedro Valerga

et al.

Abstract: Nützliche mechanistische Informationen über die Cyclometallierung lassen sich aus Untersuchungen der umgekehrten Reaktion, der Protonierung des Metallacyclus 1 durch Säuren, erhalten, die in Abhängigkeit von der Koordinationsfähigkeit des Gegenions zu unterschiedlichen Produkten führt (siehe Schema). Ar = 3,5‐(F3C)2C6H3; Tf = F3CSO2.

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Cited by 28 publications

References 43 publications

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Cleavage of the Calkyl−Caryl Bond of [Pd−CH2CMe2Ph] Complexes

Cámpora¹,

Gutiérrez‐Puebla²,

López³

et al. 2001

Angew. Chem.

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The cleavage and functionalization of strong CÀC single bonds [1] by transition metal compounds is an important transformation, [2±6] which is relevant to Ziegler ± Natta catalysis [7] and to other organometallic processes. [8, 9] Aryl elimination by activation of a b-C alkyl ÀC aryl bond [5] is the microscopic reverse of the migratory insertion of an alkene into a MÀC aryl bond, a relevant step of the Heck reaction [8] and of the SHOP process. [9] Herein we report on the conversion of a [PdÀCH 2 CMe 2 Ph] moiety into the corresponding phenyl derivative, [Pd À Ph] , and the subsequent functionalization of the latter by conventional C 2 H 4 migratory insertion chemistry to produce C 6 H 5 CHCH 2 .

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Cleavage of the Calkyl−Caryl Bond of [Pd−CH2CMe2Ph] Complexes

Cámpora¹,

Gutiérrez‐Puebla²,

López³

et al. 2001

Angew. Chem.

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Intramolecular C−H Activation by Alkylpalladium(II) Complexes: Insights into the Mechanism of the Palladium-Catalyzed Arylation Reaction

Martín‐Matute¹,

Mateo²,

Cárdenas³

et al. 2001

Chem. Eur. J.

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The cyclization of [ArOCH2PdL2Cl] complexes proceeds at room temperature in CH3CN in the presence of base, such as KOPh or carbonate, to form palladacycles. The effect of substituents on the aryl moiety (p-MeO > H >p-NO2) is as expected for an electrophilic aromatic substitution by electrophilic Pd(II). The absence of isotopic effect is also consistent with this proposal. Cyclopalladation proceeds with bidentate ligands (dppf, COD and phen); although the C-H activation reactions are slower in these cases. The starting [ArOCH2Pd(PPh3)2Cl] and [ArOCH2Pd(PPh3)Cl]2 complexes were prepared by transmetalation of organostannanes [(ArOCH2)4Sn] with [Pd(PPh3)2Cl2] or [Pd(PPh3)Cl2]2, respectively. Cleavage of palladacycles with HCl also gave [ArOCH2PdL2Cl] complexes.

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Catalytic Dehydrogenation of o‐Alkylated or o‐Alkoxylated Iodoarenes with Concomitant Hydrogenolysis

Motti

Catellani

2008

Adv Synth Catal

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Spaltung von Palladiummetallacyclen mit Säure: ein Sensor zum Studium der Cyclometallierung

Cited by 28 publications

References 43 publications

Cleavage of the Calkyl−Caryl Bond of [Pd−CH2CMe2Ph] Complexes

Cleavage of the Calkyl−Caryl Bond of [Pd−CH2CMe2Ph] Complexes

Intramolecular C−H Activation by Alkylpalladium(II) Complexes: Insights into the Mechanism of the Palladium-Catalyzed Arylation Reaction

Catalytic Dehydrogenation of o‐Alkylated or o‐Alkoxylated Iodoarenes with Concomitant Hydrogenolysis

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