317834-53-0Relevant articles and documents
Very small (3-6 atoms) gold cluster catalyzed carbon-carbon and carbon-heteroatom bond-forming reactions in solution
Oliver-Meseguer, Judit,Leyva-Perez, Antonio,Corma, Avelino
, p. 3509 - 3515 (2013)
Clusters get the gold: Atomic gold clusters Aun (n=3'6) are very active species (submol) for gold atalyzed carbon'carbon and carbon heteroatom bond forming reactions of interest in organic synthesis. The gold clusters can be formed insitu or generated exsitu and introduced into the reaction media. Salts, complexes, and nanoparticles (NPs) can be used as a starting source of gold. Ts=para toluenesulfonyl. Copyright
1,2,3-triazole as a special "X-factor" in promoting hashmi phenol synthesis
Chen, Yunfeng,Yan, Wuming,Akhmedov, Novruz G.,Shi, Xiaodong
, p. 344 - 347 (2010)
(Figure presented) 31PNMR experiments revealed rapid decomposition of the Ph3PAu+TfO- complex In the presence of the furan-yne, which resulted In poor reactivity as reported In the literature. Therefore, instead
Gold catalysis: On the phenol synthesis
Hashmi, A. Stephen K.,Frost, Tanja M.,Bats, Jan W.
, p. 3769 - 3771 (2001)
Figure presented For the gold-catalyzed phenol synthesis an intramolecular migration of the oxygen atom was proven. Several other late transition metals with d8 configuration allow this conversion, providing evidence for Au(III) being a catalytically active species. On the other hand gold was still the most active catalyst and gives the cleanest conversion. With additional alkynyl substituents another ring could be closed to provide doubly annellated arenes.
Gold catalysis: Proof of arene oxides as intermediates in the phenol synthesis
Hashmi, A. Stephen K.,Rudolph, Matthias,Weyrauch, Jan P.,Woelfle, Michael,Frey, Wolfgang,Bats, Jan W.
, p. 2798 - 2801 (2005)
(Chemical Equation Presented) An elusive intermediate in the gold-catalyzed phenol synthesis was elucidated by modifying the energy profile of this process. Thus, the use of a ligand based on 2-hydroxymethylpyridine enabled the first observation of the in
A recyclable polystyrene-supported gold(I) catalyst
Cao, Wenjie,Yu, Biao
, p. 1903 - 1907 (2011)
A polystyrene-(benzotriazole)(triphenylphosphine)gold(I) [Btz·Au(I)PPh3] resin, representing the first polystyrene-immobilized homogeneous gold(I) complex, was conveniently prepared, and showed remarkable catalytic activities and recyclability in three model transformations, including the tandem 3,3-rearrangement and Nazarov reaction of an enynyl acetate, the cyclization of a 1,6-enyne, and the rearrangement of an alkyne-furan. Copyright
Gold catalysis: The benefits of N and N,O ligands
Hashmi, A. Stephen K.,Weyrauch, Jan P.,Rudolph, Matthias,Kurpejovic, Elzen
, p. 6545 - 6547 (2004)
The golden key: The use of N and N,O ligands for gold(III) complexes leads to stable catalysts that facilitate an efficient synthesis of tetrahydroisoquinolines with substitution patterns difficult to access by classic methods (see picture). (Chemical equ
Solid-supported nitrogen acyclic carbene (SNAC) complexes of gold: Preparation and catalytic activity
T?upova, Svetlana,Cadu, Alban,Carabineiro, Sónia A.C.,Rudolph, Matthias,Hashmi, A. Stephen K.
, p. 97 - 102 (2017)
A readily accessible route to obtain solid-supported nitrogen acyclic carbene (SNAC) complexes of gold was designed using flow chemistry, and an analogous homogeneous gold complex was synthesized for comparison. Both were screened for counter ions in order to perform the Hashmi phenol synthesis. A recyclability study was performed on the SNAC complex, which showed the high stability of this catalyst, with no observed leaching or gold nanoparticle formation. XPS analysis was employed to confirm the presence of gold and its oxidation state.
Access to Unsymmetrically Substituted Diaryl Gold N-Acyclic Carbene (NAC) and N-Heterocyclic Carbene (NHC) Complexes via the Isonitrile Route
Vethacke, Vanessa,Claus, Vanessa,Dietl, Martin C.,Ehjeij, Daniel,Meister, Arne,Huber, Jonas F.,Paschai Darian, Leon K.,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
, p. 536 - 554 (2021/10/20)
A variety of unsymmetric diaryl gold N-acyclic carbene (NAC) complexes was synthesized via the isonitrile route by three different methods: (a) solvent free in a melt, (b) mechanochemically and (c) in THF at room temperature. The latter method can also be used to synthesize unsaturated gold NHC complexes. These methods overall offer access to a broad array of new complexes and remove one of the previous limitations of the isonitrile route to NAC and NHC complexes of gold, namely the inability to react with the less nucleophilic aromatic amines. The new complexes also proved to be successful as pre-catalysts in the gold-catalyzed phenol synthesis. (Figure presented.).
Water Can Accelerate Homogeneous Gold Catalysis
Hashmi, A. Stephen K.,Rudolph, Matthias,Stein, Philipp M.
, p. 4264 - 4271 (2021/08/03)
A selection of gold-catalyzed reactions was examined in a kinetic study on the influence of water on the rate constant. Two intramolecular reactions and one intermolecular reaction, which proceed via proton transfer and/or protodeauration steps, were inve
From Furan-Yne Systems to para -Benzoquinone Derivatives: Gold-Catalyzed Cyclization and Oxidation, and Further Reduction by Sodium Dithionate
Ahmadi, Saman,Ghanbari, Mohammad
, p. 775 - 784 (2020/10/13)
A series of furan-yne systems were transformed into the corresponding para -benzoquinone derivatives by gold(ΙΙΙ) catalyst. The two-step procedure consisted of a phenol synthesis and subsequent oxidation with iodobenzene diacetate. The reactions can be carried out in a one-pot procedure with the same precatalyst. The para -benzoquinone could simply be converted into the corresponding hydroquinones by reduction with sodium dithionate. This protocol features high efficiency, mild conditions, and wide substrate scopes.
