Stable gold(III) catalysts by oxidative addition of a carbon–carbon bond

Wu, Chung‐Yeh; Horibe, Takahiro; Jacobsen, Christian; Toste, F. Dean

doi:10.1038/nature14104

Cited by 265 publications

(208 citation statements)

References 47 publications

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“…20 6 ] have been optimized computationally at the same level of theory as that used for 1-Cl and [1] + (basis set for F 6-31+g(d′)) ( Figure 7). The lengthening of the Sb−Au bond observed experimentally on going from 3-Cl to [3-OH 2 ] + and [3] + is nicely reproduced computationally with distances of 2.76(6), 2.82(4), and 2.87(1) Å for these three compounds, respectively.…”

Section: Journal Of the American Chemical Societymentioning

confidence: 99%

Activation of a Hydroamination Gold Catalyst by Oxidation of a Redox-Noninnocent Chlorostibine Z-Ligand

2015

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In search of new platforms that support redox-controlled catalysis, we have investigated the noninnocent behavior of chlorostibine ligands coordinated to gold. The gold chlorostibine complex ((o-(Ph2P)C6H4)2SbCl)AuCl (1-Cl) undergoes a clean oxidation reaction on treatment with PhICl2. This oxidation reaction affords the corresponding trichlorostiborane complex ((o-(Ph2P)C6H4)2SbCl3)AuCl (2-Cl), which can be converted into the more tractable trifluoride analogue ((o-(Ph2P)C6H4)2SbF3)AuCl (3-Cl) by treatment with a fluoride source. As supported by experimental and computational results, these complexes possess a Au→Sb donor-acceptor interaction which is distinctly stronger in the oxidized complexes 2-Cl and 3-Cl. Both 1-Cl and 3-Cl undergo a clean chloride abstraction reaction to afford the corresponding cationic gold species [((o-(Ph2P)C6H4)2SbCl)Au](+) ([1](+)) and [((o-(Ph2P)C6H4)2SbF3)Au](+) ([3](+)), which have been isolated as SbF6(-) salts. As a result of a stronger Au→Sb interaction, cation [3](+) features a more Lewis acidic gold center. It forms an isolable water adduct and also activates terminal alkynes toward hydroamination with arylamines. These results demonstrate that the redox state of noninnocent Z-ligands can be used to control the catalytic activity of the adjoining metal center.

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Section: Journal Of the American Chemical Societymentioning

confidence: 99%

Activation of a Hydroamination Gold Catalyst by Oxidation of a Redox-Noninnocent Chlorostibine Z-Ligand

2015

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“…[222] (a) Insertion of [(IPr)Au] + into the CÀCb ond of biphenylene, (b) insertion of [(DPCb)Au] + into the CÀCbondofb iphenylene, and (c) insertion of [(DPCb)Au] + into the C aryl ÀCO and C alkyl ÀCO bondso fb enzocyclobutenone. Strain and ligand environment induced oxidativea ddition of Au I complexest ot he CÀCand CÀCO bonds of biphenylene and benzocyclobutenone.…”

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

confidence: 99%

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

Nijamudheen

Datta

2019

Chemistry A European J

153

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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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“…[98] Unlike with other methods, no external oxidants or harsh reaction conditions were required to obtain 107,w hich was isolated as ay ellow powder in 80 %y ield (Scheme 30). [98] Unlike with other methods, no external oxidants or harsh reaction conditions were required to obtain 107,w hich was isolated as ay ellow powder in 80 %y ield (Scheme 30).…”

Section: [(C^c)au(x)(y)] Complexesmentioning

confidence: 99%

Cyclometalated Gold(III) Complexes: Synthesis, Reactivity, and Physicochemical Properties

2017

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This Review showcases the ability of bi- and tridentate ligands to stabilize gold in high oxidation states through the formation of mono- and biscyclometalated gold(III) complexes. In-depth studies on the synthesis, intrinsic reactivity, catalytic relevance, and photophysical properties of stabilized gold(III) species have been carried out, setting the stage for exciting developments in various research areas, such as catalysis, inorganic and bioinorganic chemistry, ligand design, and materials science.

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Stable gold(III) catalysts by oxidative addition of a carbon–carbon bond

Cited by 265 publications

References 47 publications

Activation of a Hydroamination Gold Catalyst by Oxidation of a Redox-Noninnocent Chlorostibine Z-Ligand

Activation of a Hydroamination Gold Catalyst by Oxidation of a Redox-Noninnocent Chlorostibine Z-Ligand

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

Cyclometalated Gold(III) Complexes: Synthesis, Reactivity, and Physicochemical Properties

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