CO‐Extrusion in der homogenen Gold‐Katalyse: Reaktivität von Goldacyl‐Spezies, erzeugt durch Wasser‐Addition an Goldvinylidene

Bucher, Janina; Stößer, Tim; Rudolph, Matthias; Röminger, Frank; Hashmi, A. Stephen K.

doi:10.1002/ange.201409859

Cited by 33 publications

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References 44 publications

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“…By means of dual gold catalysis, new highly reactive intermediates prone for fruitful downstream reactions are feasible. If 1,5‐diynes incorporated in a phenylene backbone are employed, a 5‐ endo ‐ dig ‐cyclization via the β‐carbon atom of the acetylide moiety as nucleophilic centre leads to the generation of gold vinylidenes II (Scheme , top left ) –,,,,,. These highly electrophilic species were shown to react even with unactivated C( sp 2 )–H as well as C( sp 3 )–H bonds.…”

Section: Methodsmentioning

confidence: 99%

On the Gold‐Catalyzed Generation of Phenyl Cations from 1,5‐Diynes

et al. 2017

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cis-Enediyne systems bearing twon onterminal alkyne functionalitiesw ere transformed in the presence of ag oldc atalyst. As elective6 -endodig-cyclization generates mono-aurated phenyl cation intermediates,h ighe nergy species that are able to activate even primary sp 3 -C-H-bonds. Via insertion into intramolecularly offered, unactivated C-H-bonds, penta-substituted benzene derivatives are obtaineda sf inalp roducts. In most casess elective insertions into the g-sp 3 -C-H bonds of the offered tethers were observed. Scheme 1. Reported chemistry of diynes and plannedaccess to intermediate VIII.

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Section: Methodsmentioning

confidence: 99%

On the Gold‐Catalyzed Generation of Phenyl Cations from 1,5‐Diynes

et al. 2017

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Dual Gold Catalysis: Synthesis of Fluorene Derivatives from Diynes

et al. 2016

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Abstract1,5‐Diyne systems bearing one terminal and one benzyl‐ or allyl‐substituted alkyne attached to an aromatic backbone were converted in the presence of a gold catalyst. In a dual gold‐catalyzed process, gold vinylidenes are formed that selectively undergo formal CH insertion into the C(sp2)–H bond of the offered unsaturated systems. If H atoms are present in the propargylic position, a subsequent isomerization to the aromatic system takes place leading to 9H‐fluorene and 11H‐benzo[b]fluorene derivatives as final products. In the case of a quaternary carbon in the propargylic position no further aromatization is observed and 10H‐benzo[b]fluorene derivatives are obtained in high yield.magnified image

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Accessing Indenoazulenes via a Gold‐Catalysed Cyclisation of Cycloheptatrienyl‐Substituted 1,5‐Diynes

Mackenroth,

Ahrens,

Wunsch

et al. 2023

Adv Synth Catal

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Herein we report that cycloheptatrienyl‐substituted 1,5‐diynes with aromatic backbones undergo a gold‐catalysed 5‐endo‐dig cyclisation to give 11H‐indeno‐[2,1‐a]azulenes at room temperature. This methodology complements the established range of aromatic structures obtained from gold‐catalysed conversions of differently substituted 1,5‐diynes accessed via highly reactive cationic intermediates. We have demonstrated the scope of the reaction and have assessed the possibility of further functionalisation of the indenoazulene scaffold. Additionally, we have studied the optical and electrochemical properties as well as the frontier molecular orbitals of this structural motif by both spectroscopic and theoretical means.

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CO‐Extrusion in der homogenen Gold‐Katalyse: Reaktivität von Goldacyl‐Spezies, erzeugt durch Wasser‐Addition an Goldvinylidene

Cited by 33 publications

References 44 publications

On the Gold‐Catalyzed Generation of Phenyl Cations from 1,5‐Diynes

On the Gold‐Catalyzed Generation of Phenyl Cations from 1,5‐Diynes

Dual Gold Catalysis: Synthesis of Fluorene Derivatives from Diynes

Accessing Indenoazulenes via a Gold‐Catalysed Cyclisation of Cycloheptatrienyl‐Substituted 1,5‐Diynes

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