- Aqueous α-Arylation of Mono- and Diarylethanone Enolates at Low Catalyst Loading
-
Acetophenone and deoxybenzoin derivatives are selectively α-arylated using a combination of very small amounts of palladium acetate and diphenylphosphine oxide as catalyst system and water as the only solvent. Target di- and triarylethanones are isolated virtually free of metal residues, and the reaction is amenable to gram-scale. A mechanistic proposal based on TEM images, poisoning experiments, kinetic plot and ESI-MS spectrometry is also provided. (Figure presented.).
- Astarloa, Iratxe,SanMartin, Raul,Herrero, María Teresa,Domínguez, Esther
-
supporting information
p. 1711 - 1718
(2018/03/21)
-
- Aerobic dehydrogenative α-diarylation of benzyl ketones with aromatics through carbon-carbon bond cleavage
-
Substituted benzyl ketones reacted with aromatics in the presence of K 2S2O8 in CF3COOH at room temperature, yielding α-diaryl benzyl ketones through a carbon-carbon bond cleavage. In the reaction, two new carbon-carbon bonds were formed and one carbon-carbon bond was cleaved. It is very interesting that two different nucleophiles such as benzyl ketones and aromatics were coupled together without metal, which is unusual in organic synthesis.
- More, Nagnath Yadav,Jeganmohan, Masilamani
-
supporting information
p. 804 - 807
(2014/03/21)
-
- Towards a facile synthesis of triarylethanones: Palladium-catalyzed arylation of ketone enolates under homogeneous and heterogeneous conditions
-
The palladium-catalyzed regioselective α-monoarylation of deoxybenzoins and α,α-diarylation of acetophenones provides general, efficient access to 1,2,2-triarylethanones. After a comprehensive search for suitable experimental conditions to optimize such transformations, both reactions are alternatively conducted by means of either commercially available polymer-anchored catalysts or a very simple homogeneous catalytic system, thus avoiding the use of complex ligands. In addition, the synthesis of deoxybenzoins employing polymer-supported fibrous palladium catalysts is reported for the first time, and the excellent catalyst recycling properties suggest applicability to industrial purposes.
- Churruca, Fátima,SanMartin, Raul,Carril, Mónica,Tellitu, Imanol,Domínguez, Esther
-
p. 2393 - 2408
(2007/10/03)
-
- Regioselective diarylation of ketone enolates by homogeneous and heterogeneous catalysis: Synthesis of triarylethanones
-
A novel, one-step approach to 1,2,2-triarylethanones is achieved by an efficient palladium-catalyzed α,α-diarylation of commercially available acetophenones. After assaying an array of experimental conditions, two convenient procedures, which avoid ortho-arylation side reactions, are chosen to perform the target regioselective diarylation. The former protocol is based on the use of such a simple homogeneous system as Pd(OAc)2/PPh3/Cs2CO3, and the latter one employs a commercially available polymer-anchored catalyst, FibreCat 1026.
- Churruca, Fátima,SanMartin, Raul,Tellitu, Imanol,Domínguez, Esther
-
p. 5925 - 5929
(2007/10/03)
-
- Palladium-catalyzed arylation of ketone enolates: an expeditious entry to tamoxifen-related 1,2,2-triarylethanones.
-
[reaction: see text]. After a rigorous study on the effect of several catalytic systems, a simple, high yielding procedure for the preparation of 1,2,2-triarylethanones, skeletal analogues of tamoxifen, is presented. Apart from the economic and environmen
- Churruca, Fatima,SanMartin, Raul,Tellitu, Imanol,Dominguez, Esther
-
p. 1591 - 1594
(2007/10/03)
-