Arenediazonium salts as electrophiles for the oxidative addition of gold(<scp>i</scp>)

Asomoza‐Solís, Eric Omar; Rojas-Ocampo, Jonathan; Toscano, Rubén A.; Porcel, S.

doi:10.1039/c6cc03105f

Cited by 54 publications

(41 citation statements)

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“…During these reactions, the orthogonal and complimentary activitieso ft he second metal compared with Au furnishes the unique activity and selectivity trends. [212,213] Zhu et al have developed ac o-operative Au/Ag-catalyzed selectivec ross-dehydrogenative arylation of pyrazoles (Scheme 30) with fluoroarenes. [208][209][210] Pd is the redox-activec ross-coupling catalystt hat undergoes both oxidative addition and reductive elimination cascades.O nt he contrary,afew studies have utilized Ag additives to assist homogeneous Au-catalyzed crosscoupling reactions.…”

Section: Cooperative Au/m (M = Ag or Pd) Bimetallic Cross-coupling Rementioning

confidence: 99%

“…However, the mechanisms of bpy-assisted N 2 extrusion process are not Scheme37. [213] The Au III intermediates could readily undergo cross-couplingr eactions with in situ generated Ag-acetylides. [233] Scheme38.…”

Section: Oxidant-free Oxidative Addition Of C-heteroatom Bonds To Au mentioning

confidence: 99%

“…[242] The highly electron-deficient thiolatel igands stabilized the Au III complex formed. [213] Scheme44. Through as eries of articles, Amgoune, Bourissou, and co-workers have established methodologies for mild oxidative addition of disilanes to Au I complexes.…”

Section: Oxidant-free Oxidative Addition Of Eàe(e= S Si Sn Etc) Bmentioning

confidence: 99%

See 2 more Smart Citations

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Nijamudheen

Datta

2019

Chemistry A European J

145

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Transition-metal-catalyzed cross-couplingr eactions are central to many organic synthesis methodologies. Traditionally,P d, Ni, Cu, and Fe catalysts are used to promote these reactions. Recently,m any studies have showedt hat both homogeneous and heterogeneous Au catalysts can be used for activating selective cross-coupling reactions.H ere, an overview of the past studies, current trends, andf uture directions in the field of gold-catalyzed coupling reactions is presented.D esign strategiest oa ccomplish selective homocoupling and cross-coupling reactions under both homogeneous and heterogeneous conditions, computational and ex-perimental mechanistic studies, and their applicationsi nd iverse fields are critically reviewed. Specific topics covered are:o xidant-assisted and oxidant-free reactions;s train-assisted reactions;d ual Au and photoredoxc atalysis;b imetallic synergistic reactions;m echanismso fr eductivee limination processes;e nzyme-mimicking Au chemistry;c lustera nd surface reactions;a nd plasmonic catalysis. In the relevant sections, theoretical and computational studies of Au I /Au III chemistry are discussed and the predictionsf rom the calculationsa re compared with the experimental observations to derive useful design strategies.A. Nijamudheen earnedh is PhD from IACS, Kolkata,i n2 015. Currently,h ei sapostdoctoral researcher atF loridaS tate University.H is researchi nterests are in computational catalysis, solar energym aterials, and beyond Li-ion battery technologies.Ayan Dattai sc urrently aP rofessor at IACS, Kolkata.H is research interests include theoretical and computational studieso ft ransitionmetal-catalyzed reactions,o pto-electronic properties of organic and solid-statem aterials, and the design of renewableenergymaterials. He has won several awards including the DST-SERB Distinguished Investigator Award (DIA) in 2019.

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Section: Cooperative Au/m (M = Ag or Pd) Bimetallic Cross-coupling Rementioning

confidence: 99%

Section: Oxidant-free Oxidative Addition Of C-heteroatom Bonds To Au mentioning

confidence: 99%

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Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Nijamudheen

Datta

2019

Chemistry A European J

145

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“…Recently, Glorius and Toste, among others, have contributed an facile route to reactive Ar-Au III intermediates in the presence of Ru-based photosensitizer, not needing external strong oxidants. [27][28][29][30][31][32][33][34][35][36] In 2016, we developed the first photosensitizer-free, photochemical generation of Ar-Au III species from diazonium salts and gold(I)-complexes, including catalytic transformations. [37][38][39] Herein we report a visible-light-induced gold-catalyzed redox-neutral arylation of mechanistically discriminative B,Si bimetallic coupling reagents (B-Ar-Si) with diazonium salts (Scheme 1 c); mechanistic studies demonstrate that photosensitizer-free conditions are superior to gold/Ru-(bpy) 3 Cl 2 dual catalysis.…”

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confidence: 99%

Light‐Induced Gold‐Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates

et al. 2018

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Organoboron compounds are versatile synthetic building blocks. We herein report a new strategy, a photochemical gold-catalyzed chemo-selective Hiyama arylation of B,Si bifunctionalized reagents with diazonium salts, which is orthogonal to common strategies and therefore a unique tool for synthesis of valuable biarylboronates. With this new methodology a wide array of diversely functionalized sp 2and sp 3 -hybridized biarylboronates were obtained. Notably, the synergism of gold catalysis with copper catalysis or palladium catalysis, allows for one-pot iterative CÀX (heteroatom) and CÀC couplings for the rapid assembly of several simple fragments to relatively complex molecules. Mechanistic studies indicated that photosensitizer-free conditions were superior to gold/Ru(bpy) 3 Cl 2 dual catalysis. Scheme 1. Strategies for the synthesis of biarylboronates.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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“…[3] 2016 entwickelte García-Domínguez und Nevado eine Au/Pd bimetallische Katalyse,d ie zwei unabhängige Katalysezyklen beinhaltet. [5] Einige Herausforderungen erschweren die Entwicklung eines bimetallischen katalytischen Prozesses mit Au I /Au III -Katalysezyklus.E inmal aufgrund des hohen Oxidationspotentials,A u III -Zwischenstufen sind normalerweise instabil, was eine nachfolgende Tr ansmetallierung mit einer weiteren katalytischen Organometall-Spezies verhindert. In Kontrast dazu, sind bimetallische Prozesse mit Au I /Au III -Katalysezyklen kaum untersucht.…”

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Duale Gold/Silber‐Katalyse über oxidative Addition zu Alkinylgold(III)‐Zwischenstufen und silberkatalysierte C‐H‐Aktivierung für die direkte Alkinylierung von Cyclopropenen

et al. 2019

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Während goldkatalysierte synergistische katalytische Prozesse,d ie Transmetallierung mit anderen Metallen einbeziehen, gut verstanden sind, sind Au I /Au III -Zyklen in diesen Reaktionen sehr selten. Hier wird eine goldkatalysierte direkte Alkinylierung von Cyclopropenen über zwei aktive Katalysezyklen ermçglicht, ein oxidativer Katalysezyklus mit einem über oxidative Addition gebildeten Alkinyl-Au III -Komplex, und eine silbervermittelte C-H-Aktivierung. Schema 1. Bereits bekannte Au/M-bimetallische Katalyse und die hier neu vorgestellte Au/Ag-bimetallische Katalyse.

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Arenediazonium salts as electrophiles for the oxidative addition of gold(i)

Cited by 54 publications

References 54 publications

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Light‐Induced Gold‐Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates

Duale Gold/Silber‐Katalyse über oxidative Addition zu Alkinylgold(III)‐Zwischenstufen und silberkatalysierte C‐H‐Aktivierung für die direkte Alkinylierung von Cyclopropenen

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