Transmetalation of arylpalladium and platinum complexes. Mechanism and factors to control the reaction

Suzaki, Yuji; Yagyu, Takeyoshi; Osakada, Kohtaro

doi:10.1016/j.jorganchem.2006.05.064

Cited by 28 publications

(22 citation statements)

References 68 publications

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“…It is thus desirable to observe and manipulate the bimetallic intermediates from which they occur. Along these lines, the group of Osakada3a–c reported hydroxy‐bridged dinuclear phenylplatinum(II) complexes that undergo anion‐induced transmetalation. In addition, Komiya3d–f reported several heterobimetallic complexes promoting methyl or aryl group transfer from platinum; these reactions are best described as reductive eliminations involving the reduction of Pt II to Pt 0 or of Pt IV to Pt II .…”

Section: Methodsmentioning

confidence: 99%

Transmetalation Supported by a Pt^IICu^I Bond

et al. 2010

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Section: Methodsmentioning

confidence: 99%

Transmetalation Supported by a Pt^IICu^I Bond

et al. 2010

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“…We also selectively synthesized [10]CPP starting from L‐shaped cis ‐coordinated p‐ iodobiphenyl 20m by applying a protocol developed by Osakada and co‐workers . Thus, 20m was treated with a stoichiometric amount of Pd(dba) 2 (dba refers to dibenzylideneacetone) and 2,2′‐bipyridyl (bpy); the resulting intermediate was further treated with a stoichiometric amount of AgBF 4 .…”

Section: Synthesis Of Cppsmentioning

confidence: 99%

“…A plausible mechanism for the formation of [10]CPP from 20m involves oxidative addition of 20m to a Pd(dba) 2 /bpy species to afford the corresponding aryl–Pd(II) complex 20n (L′ may be cod or bpy). The cationic Pd complex generated from 20n upon treatment with silver salt induces an aryl‐coupling reaction to give trimer 21 , from which elimination of 4,4′‐bispalladium biphenyl occurs to give triangular trinuclear platinum complex 22 . Finally, reductive elimination of platinum from 22 gives [10]CPP.…”

Section: Synthesis Of Cppsmentioning

confidence: 99%

Organoplatinum‐Mediated Synthesis of Cyclic π‐Conjugated Molecules: Towards a New Era of Three‐Dimensional Aromatic Compounds

Yamago

Kayahara

Iwamoto

2014

The Chemical Record

226

221

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This article describes the most recent developments in the synthesis of three-dimensional π-conjugated molecules and the elucidation of their properties made by our research group. Various cycloparaphenylenes (CPPs) of different sizes and a cage-like 3D molecule were synthesized based on the platinum-mediated assembly of π-units and subsequent reductive elimination of platinum. The assembly of π-units by this method mimics the self-assembly process for the formation of supramolecular ligand-metal complexes with 3D cages and polyhedral structures. Furthermore, reductive elimination of platinum successfully took place with high efficiency, despite the high strain energy of the target molecule. Several size-dependent physical properties of CPPs, namely the photophysical, redox, and host-guest chemistries, were also clarified. These results are of use for a molecular-level understanding of CNT physical properties as well as fullerene peapods. Theoretical and electrochemical studies suggest that small CPPs and their derivatives should be excellent lead compounds for molecular electronics.

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“…[23] Recently, Grushin et al have reported the clever use of ligand disproportionation of Pd II complexes as a method to access otherwise elusive trans-difluoro-palladium complexes (Scheme 8). [24] The driving force of the reaction is the irreversible PhÀPh coupling.…”

Section: Introductionmentioning

confidence: 99%

Bimetallic Catalysis using Transition and Group 11 Metals: An Emerging Tool for CC Coupling and Other Reactions

Pérez‐Temprano

Casares

Espinet

2012

Chemistry A European J

214

131

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Bimetallic catalysis refers to homogeneous processes in which either two transition metals (TM), or one TM and one Group 11 (G11) element (occasionally Hg also), cooperate in a synthetic process (often a C-C coupling) and their actions are connected by a transmetalation step. This is an emerging research area that differs from the isolated or tandem applications of the now classic processes (Stille, Negishi, Suzuki, Hiyama, Heck). Most of the reactions used so far combine Pd with a second metal, often Cu or Au, but syntheses involving very different TM couples (e.g., Cr/Ni in the catalyzed vinylation of aldehydes) have also been developed. Further development of the topic will soon demand a good knowledge of the mechanisms involved in bimetallic catalysis, but this knowledge is very limited for catalytic processes. However, there is much information available, dispersed in the literature, coming from basic research on exchange reactions occurring out of any catalytic cycle, in polynuclear complexes. These are essentially the same processes expected to operate in the heart of the catalytic process. This Review gathers together these two usually isolated topics in order to stimulate synergy between the bimetallic research coming from more basic organometallic studies and the more synthetic organic approaches to this chemistry.

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Transmetalation of arylpalladium and platinum complexes. Mechanism and factors to control the reaction

Cited by 28 publications

References 68 publications

Transmetalation Supported by a Pt^IICu^I Bond

Transmetalation Supported by a Pt^IICu^I Bond

Organoplatinum‐Mediated Synthesis of Cyclic π‐Conjugated Molecules: Towards a New Era of Three‐Dimensional Aromatic Compounds

Bimetallic Catalysis using Transition and Group 11 Metals: An Emerging Tool for CC Coupling and Other Reactions

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Transmetalation of arylpalladium and platinum complexes. Mechanism and factors to control the reaction

Cited by 28 publications

References 68 publications

Transmetalation Supported by a PtIICuI Bond

Transmetalation Supported by a PtIICuI Bond

Organoplatinum‐Mediated Synthesis of Cyclic π‐Conjugated Molecules: Towards a New Era of Three‐Dimensional Aromatic Compounds

Bimetallic Catalysis using Transition and Group 11 Metals: An Emerging Tool for CC Coupling and Other Reactions

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Product

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Transmetalation Supported by a Pt^IICu^I Bond

Transmetalation Supported by a Pt^IICu^I Bond