Synthesis, structure and reactivity of organogold compounds of relevance to homogeneous gold catalysis

Hashmi, A. Stephen K.; Ramamurthi, Tanuja Dondeti; Röminger, Frank

doi:10.1016/j.jorganchem.2008.11.054

Cited by 277 publications

(142 citation statements)

References 37 publications

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“…They proposed transmetalation of a vinyl ligand from Au I to Au III to explain the formation of the enone dimer (Scheme 42). [99,100] The recent carboauration reactions using gold have an interesting precedent in a process reported by Shirakawa and Hayashi in 2005; that is, the arylmagnesiation of alkynes using cooperative iron and copper complexes as catalysts. The arylmagnesiation proceeds in high yields in the presence of both metal catalysts.…”

Section: Carboauration Reactions Of Alkynesmentioning

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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Section: Carboauration Reactions Of Alkynesmentioning

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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“…[52] (Tabelle 2). [53] In den Einträgen 1-4 führte die Verwendung der elektrophilen X + -Reagentien NCS, NBS, NIS und Barluengas Reagens (74) [54] zur Bildung der halogenierten Produkte 72 a-c in guten Ausbeuten. Selectfluor (66) III -Katalyse basieren, berichtet; diese setzten andere starke passive Oxidationsmittel wie PhI(OAc) 2 und tBuOOH ein.…”

Section: Introductionunclassified

“…[55][56][57][58] Zhang und Mitarbeiter entwickelten eine bedeutende Klasse von Au I -katalysierten Reaktionen, die elektrophile N-F-Reagentien als passive Oxidationsmittel nutzen, um Au I in Au III umzuwandeln und selektive reduktive Eliminierungen von C-O und C-C auszulösen (Schemata 21 und 22). [59,60] Der erste Bericht von Zhangs Gruppe hatte eine intramolekulare C-O-Bindungsbildung zum Thema, bei der Selectfluor (66) Tabelle 2: Reaktionen der [Au I -Vinyl]-Komplexe mit üblichen Halogenierungsmitteln (Hashmi et al, 2009). [53] Eintrag Elektrophil [a] X Ausb.…”

Section: Introductionunclassified

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Passive F⁺‐Oxidationsmittel ermöglichen die selektive reduktive Eliminierung hochvalenter Metallzentren in der Katalyse

et al. 2011

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Die reduktive Eliminierung teils oder vollständig oxidierter Metallzentren ist ein wichtiger Schritt in einer Unzahl von C‐C‐ und C‐Heteroatom‐Bindungsbildungen. Eine Möglichkeit, anspruchsvolle reduktive Eliminierungen zu erleichtern, besteht in der Oxidation der Metallzentren durch Zwei‐Elektronen‐Oxidationsmittel (also von Mn zu Mn+2). Viele der für diese Umwandlung typischen Oxidationsmittel enthalten allerdings Sauerstoff‐, Stickstoff‐ oder Halogenatome — die sich anschließend an der reduktiven Eliminierung beteiligen könnten —, sodass ein Produktgemisch entstehen würde. In diesem Kurzaufsatz beschreiben wir die Untersuchungen zu einem neuartigen Lösungsansatz für dieses verbreitete Problem in der metallorganischen Chemie: die Verwendung von passiven F+‐Oxidationsmitteln sowie die jüngsten Anwendungen in PdII/PdIV‐ und AuI/AuIII‐Katalysen. Außerdem besprechen wir kurz ein seltenes Beispiel, in dem die Verwendung eines Ein‐Elektronen‐Oxidationsmittels zur Begünstigung einer selektiven reduktiven Eliminierung bei Palladium(II)‐katalysierten C‐H‐Funktionalisierungen gezeigt werden konnte; dies sehen wir als eine vielversprechende Richtung für zukünftige Anwendungen auf diesem Gebiet an.

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“…The reaction can be catalyzed by a variety of metal-based catalytic systems [3]. Recently, gold, in spite of its inertness towards ambient conditions, has emerged as a powerful catalytic agent [4][5][6] when combined with oxidizing agents such as selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) or peracids in homogeneous phase [7][8][9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Electrochemical monitoring of the oxidative coupling of alkynes catalyzed by triphenylphosphine gold complexes

Doménech

Leyva‐Pérez

Al‐Resayes

et al. 2012

Electrochemistry Communications

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Abstract. Electrochemical monitoring of the oxidative coupling of alkynes in the homogeneous phase through catalytic cycles involving triphenylphosphine gold complexes and selectfluor as oxidant reveals that at least two gold species in +3 and +1 oxidation states are implicated. Electrochemically driven homocoupling of terminal alkynes using molecular oxygen as the oxidant can be performed using such catalysts.

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Synthesis, structure and reactivity of organogold compounds of relevance to homogeneous gold catalysis

Cited by 277 publications

References 37 publications

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

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

Passive F⁺‐Oxidationsmittel ermöglichen die selektive reduktive Eliminierung hochvalenter Metallzentren in der Katalyse

Electrochemical monitoring of the oxidative coupling of alkynes catalyzed by triphenylphosphine gold complexes

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Synthesis, structure and reactivity of organogold compounds of relevance to homogeneous gold catalysis

Cited by 277 publications

References 37 publications

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

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

Passive F+‐Oxidationsmittel ermöglichen die selektive reduktive Eliminierung hochvalenter Metallzentren in der Katalyse

Electrochemical monitoring of the oxidative coupling of alkynes catalyzed by triphenylphosphine gold complexes

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Passive F⁺‐Oxidationsmittel ermöglichen die selektive reduktive Eliminierung hochvalenter Metallzentren in der Katalyse