Gold Catalysis 2.0

Braun, Ingo; Asiri, Abdullah M.; Hashmi, A. Stephen K.

doi:10.1021/cs400437s

Cited by 242 publications

(104 citation statements)

References 26 publications

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“…Recent studies have provided strong evidence for their existence, and have demonstrated their powerful reactivity [51–55], identifying them as key players in ongoing activity developing the exciting notion of dual activation using gold catalysts [56]. …”

Section: Resultsmentioning

confidence: 99%

Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives

Morán-Poladura¹,

Rubio²,

González³

2013

Beilstein J. Org. Chem.

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SummaryAn efficient entry to the preparation of elusive 4-unsubstituted-3-iodo-2H-chromenes has been accomplished as result of a catalytic cyclization. Thus, upon exposition of [(3-iodoprop-2-yn-1-yl)oxy]arenes to IPrAuNTf2 (3 mol %), in 1,4-dioxane at 100 °C, the desired heterocyclic motif is readily assembled. This process nicely tolerates a variety of functional groups and, interestingly, it is compatible with the presence of strong electron-withdrawing groups attached to the arene. The overall transformation can be termed as a new example of a migratory cycloisomerization and, formally, it involves well-blended 1,2-iodine shift and hydroarylation steps.

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Section: Resultsmentioning

confidence: 99%

Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives

Morán-Poladura¹,

Rubio²,

González³

2013

Beilstein J. Org. Chem.

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“…Then the collected organic layers were dried over anhydrous MgSO 4 , concentrated under vacuum, and puried by column chromatography (dichloromethane/methanol ¼ 10/1) to give 28 mg of Rh-EDC (20%) as a pink solid. 1 …”

Section: Synthesis Of Rh-edcmentioning

confidence: 99%

“…Recently, using gold as a catalyst has attracted great interest in the eld of synthetic chemistry. [1][2][3][4][5] Yet, along with their synthetic utility, gold species exert diverse biological effects on human health, ranging from disease treatment to organ damage. [6][7][8][9][10] Drugs based on certain gold-ion complexes can be used to treat various human diseases, including asthma, cancer, and rheumatoid arthritis, among other autoimmune diseases.…”

Section: Introductionmentioning

confidence: 99%

A guanidinium modified rhodamine-based fluorescent probe for in vitro/vivo imaging of gold ions

2015

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“…13,14 Well-defined digold pre-catalysts are now used for a number of applications. [15][16][17][18][19][20][21][22][23] Dual gold catalysis might help to overcome the hurdle that Au I has only two coordination sites available, with a linear geometry. 24 Another issue that remains is that understanding how ligand structure affects reactivity in catalysis, although some useful empirical observations have been made.…”

Section: Introductionmentioning

confidence: 99%

The preference for dual-gold(i) catalysis in the hydro(alkoxylation vs. phenoxylation) of alkynes

et al. 2017

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This version is available at https://strathprints.strath.ac.uk/61289/ Strathprints is designed to allow users to access the research output of the University of Strathclyde. Unless otherwise explicitly stated on the manuscript, Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Please check the manuscript for details of any other licences that may have been applied. You may not engage in further distribution of the material for any profitmaking activities or any commercial gain. You may freely distribute both the url (https://strathprints.strath.ac.uk/) and the content of this paper for research or private study, educational, or not-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to the Strathprints administrator: strathprints@strath.ac.ukThe Strathprints institutional repository (https://strathprints.strath.ac.uk) is a digital archive of University of Strathclyde research outputs. It has been developed to disseminate open access research outputs, expose data about those outputs, and enable the management and persistent access to Strathclyde's intellectual output. Herein we study the hydroalkoxylation and hydrophenoxylation of alkynes using density functional theory calculations, and compare two possible mechanisms that have been proposed previously on the basis of theoretical and experimental studies, which unravel different preferences because of both the nature of the alkyne and alcohol, as well as the non-innocent role of the counter-anion of the dual gold based catalyst. Entropy is found to have a significant effect, rendering the nucleophilic attack of the monoaurated intermediate [Au(L)(η 2 -alkyne)] + difficult both kinetically and thermodynamically; this mechanism cannot easily form only the trans-alkene product that is observed experimentally. Instead, reaction via a dual gold catalysed mechanism presents much lower barriers. In addition, for the sake of direct comparison with recent results by Belanzoni, Zuccaccia, oversimplification of the Nheterocyclic carbene (NHC) ligand in the calculations might decrease the enthalpy barrier and lead to results that are not directly applicable to experiment. Moreover, the alkylic or arylic nature of the alkyne and/or alcohol is also tested. ORGANIC & BIOMOLECULAR CHEMISTRY ARTICLE

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Gold Catalysis 2.0

Cited by 242 publications

References 26 publications

Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives

Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives

A guanidinium modified rhodamine-based fluorescent probe for in vitro/vivo imaging of gold ions

The preference for dual-gold(i) catalysis in the hydro(alkoxylation vs. phenoxylation) of alkynes

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