Mechanistic and asymmetric investigations of the Au-catalysed cross-coupling between aryldiazonium salts and arylboronic acids using (P,N) gold complexes

Tabey, Alexis; Berlande, Murielle; Hermange, Philippe; Fouquet, Éric

doi:10.1039/c8cc07530a

Cited by 35 publications

(26 citation statements)

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“…Dual Au and photoredox catalyzedintramolecular( a) alkoxyarylation, [272] (b) amino-arylation, [273] and (c) ipso-arylation-cyclization [274] reactions of alkynes with aryl diazonium salts. [279] Insteado fa rylboronic acids, Patil et al utilized arylsilanes as the coupling partners for the diaryl-forming reactions. [275,276] Based on stoichiometric experiments, Fouquet et al have further investigated the mechanismsf or the cross-coupling of arylboronic acids with aryldiazonium salts and used the methodologies for enantioselective synthesis of biaryls.…”

Section: Dual Gold and Photoredox Catalysisf Or Cross-couplingr Eactionsmentioning

confidence: 99%

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

Nijamudheen

Datta

2019

Chemistry A European J

142

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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: Dual Gold and Photoredox Catalysisf Or Cross-couplingr Eactionsmentioning

confidence: 99%

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

Nijamudheen

Datta

2019

Chemistry A European J

142

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“…In 2018, Hermange, Fouquet, and co-workers reported that biaryl products could be obtained in up to 26% ee using mononuclear gold complexes bearing chiral P,N-ligands (Scheme 27a). 48 The two-step stoichiometric cross-coupling method relies on an initial transmetalation with an arylboronic acid followed by coupling with an aryldiazonium salt under photoredox conditions. In 2019, Kramer and co-workers demonstrated that stoichiometric aryl-aryl homocoupling can be achieved with up to 91% ee by using binuclear gold complexes bearing C 2 -symmetric chiral ligands (Scheme 27b).…”

Section: Discussionmentioning

confidence: 99%

Homogeneous Gold-Catalyzed Aryl–Aryl Coupling Reactions

Kramer

2020

Synthesis

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Synthesis of biaryl motifs are crucial for the development and synthesis of pharmaceuticals, natural products, and functional materials. During the last decade, gold-catalyzed aryl–aryl coupling reactions have evolved from a curiosity to a well-established research field. This review summarizes the field from early examples up to the latest developments. Facile C–H functionalization and orthogonal reactivity compared to many other types of transition metal catalysis, for example, palladium catalysis, makes gold-catalyzed aryl–aryl coupling reactions highly appealing and valuable.1 Introduction2 Early Examples3 Cross-Coupling with External Oxidants4 Cross-Coupling without External Oxidants5 Conclusions

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“…If the reaction is carried out in the absence of a light source, the N 2 ‐unit from the diazonium salt is retained and azobenzofurans are formed in moderate to high yields. Stoichiometric experiments demonstrate that these products are accessible from the same vinyl Au I intermediate and lead us to propose that the often suggested photochemical oxidative addition–––– either occurs after the formation of a vinyl Au I species or may even not involve oxidation state changes.…”

Section: Methodsmentioning

confidence: 99%

Light‐Induced Mechanistic Divergence in Gold(I) Catalysis: Revisiting the Reactivity of Diazonium Salts

et al. 2019

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Mechanistic and asymmetric investigations of the Au-catalysed cross-coupling between aryldiazonium salts and arylboronic acids using (P,N) gold complexes

Abstract: Aryldiazonium salts and arylboronic acids were coupled via three different pathways from (P,N)–AuCl complexes, with enantiomeric excesses up to 26%.

Cited by 35 publications

References 66 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

Homogeneous Gold-Catalyzed Aryl–Aryl Coupling Reactions

Light‐Induced Mechanistic Divergence in Gold(I) Catalysis: Revisiting the Reactivity of Diazonium Salts

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