- Gold(I) complexes bearing ring-fused benzoxazine-derived triazolylidenes and their use in C–N bond-forming processes
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We report the synthesis and full characterization of a novel series of ring-fused benzoxazine-derived triazolium salts (1a–c) and their corresponding triazolylidene gold(I) complexes (2a–c). All new compounds were fully characterized by means of 1H and 13C NMR spectroscopy, elemental analyses, and mass spectroscopy and in the case of triazoliums 1a and 1b by single-crystal X-ray diffraction. The new triazolylidene gold complexes (2a–c) were tested as precatalysts in the hydroamination and hydrohydrazination of terminal alkynes employing aniline derivatives and hydrazine as nitrogen sources, respectively.
- Campos-Dominguez, Emmanuel,Vasquez-Perez, Jose,Rojas-Lima, Susana,Lopez-Ruiz, Heraclio,Mendoza-Espinosa, Daniel
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- Synthesis and Catalytic Applications of Multinuclear Gold(I)-1,2,3-Triazolylidene Complexes
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A series of mono- to trinuclear gold(I) complexes (1–3) supported by oxo-functionalized 1,2,3-triazolylidenes have been prepared. All new compounds were fully characterized by means of 1H and 13C NMR spectroscopy, elemental analyses, and in the case of complexes 1 and 2 by x-ray diffraction. The catalytic performance of the new triazolylidene gold complexes was tested in several hydroelementation and cyclization processes employing a variety of alkynes as starting materials. According to the overall results, the trinuclear complex 3 displayed the highest catalytic activity in all processes, providing good to excellent yields under mild reaction conditions.
- Rendón-Nava, David,álvarez-Hernández, Alejandro,Mendoza-Espinosa, Daniel
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supporting information
p. 840 - 847
(2021/02/26)
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- Syntheses of Triangular Gold Complexes and Their Applications in Hydroamination Reaction
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Triangular all-metal complexes have aroused our research interest due to their unique structural and properties. Herein, through the facile reduction of μ3-oxo complex [μ3-O(PPh3Au)3]+BF4s
- Li, Jia,Li, Xujun,Sun, Lei,Wang, Xiaoshuang,Yuan, Lixia,Wu, Lingang,Liu, Xiang,Wang, Yanlan
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supporting information
p. 4230 - 4237
(2021/09/25)
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- Construction of Stable Metal–Organic Framework Platforms Embedding N-Heterocyclic Carbene Metal Complexes for Selective Catalysis
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We report a bottom-up approach to immobilize catalysts into MOFs, including copper halides and gold chloride in a predictable manner. Interestingly, the structures of MOFs bearing NHC metal complexes maintained a similar 4-fold interpenetrated cube. They
- Kim, Hyunyong,Kim, Hyunseok,Kim, Kimoon,Lee, Eunsung
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supporting information
p. 18687 - 18697
(2021/12/17)
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- Mono- and diylide-substituted phosphines (YPhos): Impact of the ligand properties on the catalytic activity in gold(i)-catalysed hydroaminations
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Understanding the impact of ligand properties on their performance in catalysis is seminal for future ligand design and catalyst improvement. In this work, the influence of the steric and electronic properties on the efficiency of a series of mono- and di
- Schwarz, Christopher,Handelmann, Jens,Baier, Daniel M.,Ouissa, Alina,Gessner, Viktoria H.
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p. 6808 - 6815
(2019/12/03)
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- Ylide-Functionalized Phosphines: Strong Donor Ligands for Homogeneous Catalysis
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Phosphines are important ligands in homogenous catalysis and have been crucial for many advances, such as in cross-coupling, hydrofunctionalization, or hydrogenation reactions. Herein we report the synthesis and application of a novel class of phosphines bearing ylide substituents. These phosphines are easily accessible via different synthetic routes from commercially available starting materials. Owing to the extra donation from the ylide group to the phosphorus center the ligands are unusually electron-rich and can thus function as strong electron donors. The donor capacity surpasses that of commonly used phosphines and carbenes and can easily be tuned by changing the substitution pattern at the ylidic carbon atom. The huge potential of ylide-functionalized phosphines in catalysis is demonstrated by their use in gold catalysis. Excellent performance at low catalyst loadings under mild reaction conditions is thus seen in different types of transformations.
- Scherpf, Thorsten,Schwarz, Christopher,Scharf, Lennart T.,Zur, Jana-Alina,Helbig, Andreas,Gessner, Viktoria H.
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supporting information
p. 12859 - 12864
(2018/09/25)
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- Synthesis and Catalytic Benefits of Tetranuclear Gold(I) Complexes with a C4-Symmetric Tetratriazol-5-ylidene
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The facile preparation of a C4-symmteric tetratriazolium salt and its subsequent metalation to generate a series of tetranuclear mesoionic carbene gold(I) complexes is presented. The complete structural characterization of the metallic carbenes
- Flores-Jarillo, Mariana,Mendoza-Espinosa, Daniel,Salazar-Pereda, Verónica,González-Montiel, Simplicio
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supporting information
p. 4305 - 4312
(2017/11/20)
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- Expanding the forefront of strong organic br?nsted acids: Proton-catalyzed hydroamination of unactivated alkenes and activation of au(i) for alkyne hydroamination
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The synthesis of a solid, bench-stable, strong organic Br?nsted acid with a computed pKa of 0.9 is reported. An X-ray crystal structure and DFT calculations are provided which offer insight into the bonding of this acid. The application of this
- Mirabdolbaghi, Roya,Dudding, Travis
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supporting information
p. 1930 - 1933
(2015/04/27)
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- N-heterocyclic carbenes and imidazole-2-thiones as ligands for the gold(I)-catalysed hydroamination of phenylacetylene
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Gold(I) complexes of 1-[1-(2,6-dimethylphenylimino)alkyl]-3-(mesityl) imidazol-2-ylidene (CImineR), 1,3-dimesitylimidazol-2-ylidene (IMes) and of the corresponding thione derivatives (SImineR and IMesS) were prepared and structurally
- Alvarado, Edwin,Badaj, Anna C.,Larocque, Timothy G.,Lavoie, Gino G.
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p. 12112 - 12121
(2012/10/29)
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- Palladium-catalyzed aerobic oxidative cyclization of N-aryl imines: Indole synthesis from anilines and ketones
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We report here an operationally simple, palladium-catalyzed cyclization reaction of N-aryl imines, affording indoles via the oxidative linkage of two C-H bonds under mild conditions using molecular oxygen as the sole oxidant. The process allows quick and atom-economical assembly of indole rings from inexpensive and readily available anilines and ketones and tolerates a broad range of functional groups.
- Wei, Ye,Deb, Indubhusan,Yoshikai, Naohiko
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supporting information; scheme or table
p. 9098 - 9101
(2012/07/14)
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- Indium catalyzed tandem hydroamination/hydroalkylation of terminal alkynes
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The first direct intermolecular hydroamination/hydroalkylation of terminal alkynes catalyzed by In(OTf)3 under one-pot conditions leading to the formation of conjugated ketimines in good yields is described.
- Sarma, Rupam,Prajapati, Dipak
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scheme or table
p. 9525 - 9527
(2011/10/01)
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- Synthesis and characterization of new tetra-substituted porphyrins with exo-donor carboxylic groups as building blocks for supramolecular architectures. Catalytic and structural studies of their metalated derivatives
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We report herein the synthesis of the porphyrins 5,10,15,20-tetrakis(4- carboxybiphenyl)-porphyrin (H2TCBP) and 5,10,15,20-tetrakis(4- carboxy-2,6-dimethylbiphenyl)porphyrin (H2TCDMBP) bearing diphenyl units on meso-positions, and of
- Carlucci, Lucia,Ciani, Gianfranco,Maggini, Simona,Proserpio, Davide M.,Ragaini, Fabio,Gallo, Emma,Ranocchiari, Marco,Caselli, Alessandro
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experimental part
p. 804 - 814
(2011/09/15)
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- A highly regioselective Cu-exchanged tungstophosphoric acid catalyst for hydroarylation and hydroamination of alkynes
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An efficient and reusable Cu-exchanged tungstophosphoric acid catalyst is demonstrated for the solvent free hydroarylation and hydroamination reactions of alkynes with numerous arene and amine derivatives, respectively. The catalyst exhibited exceptionally high activity and regioselectivity in both the reactions.
- Pasha, Nayeem,Seshu Babu,Venkateswara Rao,Sai Prasad,Lingaiah
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scheme or table
p. 239 - 242
(2009/05/11)
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- Polymethylhydrosiloxane (PMHS)/trifluoroacetic acid (TFA): a novel system for reductive amination reactions
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Polymethylhydrosiloxane (PMHS)/trifluoroacetic acid (TFA) was discovered as a novel metal-free system for reductive amination reactions. A variety of (het)aryl amines as well as a representative carbamate and urea were successfully alkylated by benzaldehyde in the presence of PMHS and TFA in dichloromethane at room temperature in moderate to excellent yields (28-87%). Furthermore, this reaction protocol was successfully applied to the alkylation of p-nitroaniline with a wide range of aldehydes, ketones, and a representative acetal to obtain the alkylated products in yields ranging from 40% to 92%. The current work represents one of the very few examples of PMHS being activated by a Br?nsted acid.
- Patel, Jay P.,Li, An-Hu,Dong, Hanqing,Korlipara, Vijaya L.,Mulvihill, Mark J.
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scheme or table
p. 5975 - 5977
(2010/01/18)
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- Synthesis of bifunctional Au-Sn organic-inorganic catalysts for acid-free hydroamination reactions
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Gold(III) complexes heterogenized on the surface of a Sn-containing MCM-41 are efficient recyclable catalysts for hydroamination reactions, without requiring any acid promoters. The Royal Society of Chemistry.
- Corma, Avelino,Gonzalez-Arellano, Camino,Iglesias, Marta,Navarro, M. Teresa,Sanchez, Felix
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supporting information; scheme or table
p. 6218 - 6220
(2009/05/06)
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- Development of highly enantioselective new Lewis basic N-formamide organocatalysts for hydrosilylation of imines with an unprecedented substrate profile
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l-Pipecolinic acid derived N-formamides have been developed as new Lewis basic organocatalysts that promote the asymmetric reduction of N-aryl ketimines using trichlorosilane as the reducing agent. The substituent on N4 of the piperazinyl backbone and the
- Wu, Pengcheng,Wang, Zhouyu,Cheng, Mounuo,Zhou, Li,Sun, Jian
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experimental part
p. 11304 - 11312
(2009/04/06)
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- An efficient reusable silver-exchanged tungstophosphoric acid heterogeneous catalyst for solvent-free intermolecular hydroamination of alkynes
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Hydroamination of alkynes with both aromatic and aliphatic amines proceeds efficiently in the presence of silver-exchanged tungstophosphoric acid (AgTPA) catalyst under solvent-free conditions to afford ketimines in excellent yields. The Royal Society of
- Lingaiah,Babu, N. Seshu,Reddy, K. Mohan,Prasad, P. S. Sai,Suryanarayana
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p. 278 - 279
(2007/10/03)
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- Au(I)-catalyzed highly efficient intermolecular hydroamination of alkynes
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Addition of aniline derivatives to aromatic and aliphatic alkynes proceeds efficiently in the presence of a gold(I) catalyst (0.01-1.0 mol %) to afford ketimines in good yields.
- Mizushima, Eiichiro,Hayashi, Teruyuki,Tanaka, Masato
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p. 3349 - 3352
(2007/10/03)
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- Amination of benzylic C-H bonds by aryl azides catalysed by Co(II)(porphyrin) complexes. A new reaction leading to secondary amines and imines
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Co(II)(porphyrin) complexes catalyse the reaction of aromatic azides, ArN3, with hydrocarbons containing a benzylic group, R1R2R3CH, to give the corresponding amines, R1R2R3C-NHAr. When at least one of the R1-R3 substituents is hydrogen, the catalytic reaction proceeds further to give the imines R1R2C=NAr in good yields.
- Cenini,Gallo,Penoni,Ragaini,Tollari
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p. 2265 - 2266
(2007/10/03)
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