62144-16-5Relevant academic research and scientific papers
α-Arylation of (hetero)aryl ketones in aqueous surfactant media
Gallou, Fabrice,Lipshutz, Bruce H.,Roa, Daniel E.,Wood, Alex B.
supporting information, p. 4858 - 4865 (2021/07/12)
α-Arylation reactions can be performed in water, enabled by a designer surfactant,under mild conditions and in the absence of organic co-solvents. A multitude of aryl and heteroaryl ketones are amenable to coupling with functionalized aryl halides. Use of a lipophilic base that can gain entry to the micellar inner cores mediates enolization. In some cases, palladium loadings as low as 2500 ppm (0.25 mol%) are sufficient for coupling in a completely recyclable medium, exemplifying chemistry in water.
N-Heterocyclic carbene-palladacyclic complexes: synthesis, characterization and their applications in the C-N coupling and α-arylation of ketones using aryl chlorides
Liu, Feng,Hu, Yuan-Yuan,Li, Di,Zhou, Quan,Lu, Jian-Mei
, p. 5683 - 5690 (2018/08/24)
N-Heterocyclic carbene-palladacyclic complexes 3 were successfully achieved in a one-pot procedure under mild conditions. The structure of 3a was unambiguously confirmed by X-ray single crystal diffraction and it was an active catalyst in the Buchwald-Hartwig amination and α-arylation of ketones even at very low catalyst loadings (0.01 mol%).
Novel bisamide palladium(II) pincer complexes: effective catalysts in α-arylation of ketones
Kai, Wang,Liu, Dabin,Qian, Hua,Ye, Zhiwen
, p. 443 - 450 (2017/07/12)
Three benzenedicarboxamide ligands (L) were designed and synthesized, and each was used to prepare a palladium(II) complex Pd(L)Br and Pd(L)(OAc). These NCN pincer complexes were used to catalyze the α-arylations of a variety of ketones with aryl chlorides or bromides in various solvents, and moderate-to-excellent yields were obtained (up to 95%). Further research showed that unactivated and sterically hindered aryl halides and ketones are also suitable substrates for the synthesis of α-arylation. Graphical Abstract: [Figure not available: see fulltext.].
Fe(III)-mediated isomerization of α,α-diarylallylic alcohols to ketones: Via radical 1,2-aryl migration
Deng, Ziyang,Chen, Changwei,Cui, Sunliang
, p. 93753 - 93755 (2016/10/18)
An Fe(iii)-mediated radical 1,2-aryl migration of α,α-diarylallylic alcohols for the isomerization to ketones is described. The Fe(acac)3-silane would convert the alkene to an alkyl radical and initiates a 1,2-aryl migration-oxidation process. Thus Fe(acac)3 serves as an olefin hydrogen atom transfer initiator and oxidant, while various allylic alcohols could isomerize to ketones in moderate to good yields.
Palladium-catalyzed α-arylation of arylketones at low catalyst loadings
Marelli, Enrico,Corpet, Martin,Davies, Sian R.,Nolan, Steven P.
supporting information, p. 17272 - 17276 (2015/02/05)
A general catalytic protocol for the α-arylation of aryl ketones has been developed. It involves the use of a preformed, bench-stable Pd-N-heterocyclic carbene pre-catalyst bearing IHept as an ancillary ligand, and allows the coupling of various functiona
General and mild Ni0-catalyzed α-arylation of ketones using aryl chlorides
Fernndez-Salas, Jos A.,Marelli, Enrico,Cordes, David B.,Slawin, Alexandra M.Z.,Nolan, Steven P.
supporting information, p. 3906 - 3909 (2015/10/19)
A general methodology for the α-arylation of ketones using a nickel catalyst has been developed. The new well-defined [Ni(IPr)(cin)Cl] (1c) pre-catalyst showed great efficiency for this transformation, allowing the coupling of a wide range of ketones, including acetophenone derivatives, with various functionalised aryl chlorides. This cinnamyl-based Ni-N-heterocyclic carbene (NHC) complex has demonstrated a different behaviour to previously reported NHC-Ni catalysts. Preliminary mechanistic studies suggest a Ni0/NiII catalytic cycle to be at play.
(N-Heterocyclic Carbene)-Pd-catalyzed anaerobic oxidation of secondary alcohols and domino oxidation-arylation reactions
Landers, Brant,Berini, Christophe,Wang, Chao,Navarro, Oscar
experimental part, p. 1390 - 1397 (2011/05/02)
The use of commercially available (SIPr)Pd(cinnamyl)Cl (SIPr = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene) as a precatalyst for the anaerobic oxidation of secondary alcohols is described. The use of this complex allows for a drastic reduction in the reaction times and catalyst loading when compared to the unsaturated counterpart. This catalytic system is compatible with the use of microwave dielectric heating, decreasing even further catalyst loading and reaction times. Domino Pd-catalyzed oxidation-arylation reactions of secondary alcohols are also presented.(Figure Presented)
NUCLEOPHILIC HETEROCYCLIC CARBENE DERIVATIVES OF PD(ACAC)2 FOR CROSS-COUPLING REACTIONS
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Page/Page column 15, 31-32, (2010/11/25)
Embodiments in accordance with the present invention provide for a palladium complex characterized by the general Formula (I): where A is a bidentate monoanionic ligand, NHC is a nucleophilic heterocyclic carbene, and Z is an anionic ligand. Such palladium complexes are useful in initiating cross-coupling reactions.
Suzuki-Miyaura, α-ketone arylation and dehalogenation reactions catalyzed by a versatile N-heterocyclic carbene-palladacycle complex
Navarro, Oscar,Marion, Nicolas,Oonishi, Yoshihiro,Kelly III, Roy A.,Nolan, Steven P.
, p. 685 - 692 (2007/10/03)
The activity of the complex (IPr)PdCl(η2-N,C-C 12H7NMe2), 1 [IPr = (N,N′-bis(2,6- diisopropylphenyl)-imidazol)-2-ylidene], in the Suzuki-Miyaura cross-coupling reaction involving unactivated aryl chlorides and triflates with arylboronic acids at room temperature in technical grade 2-propanol is described. These conditions allow for the synthesis of di- and tri-ortho-substituted biaryls in very short reaction times. This complex also displays very high activity for α-ketone arylation and dehalogenation reactions of activated and unactivated aryl chlorides.
Synthesis of novel (NHC)Pd(acac)Cl complexes (acac=acetylacetonate) and their activity in cross-coupling reactions
Navarro, Oscar,Marion, Nicolas,Scott, Natalie M.,González, Juan,Amoroso, Dino,Bell, Andrew,Nolan, Steven P.
, p. 9716 - 9722 (2007/10/03)
The synthesis and characterization of two new complexes (IPr)Pd(acac) 2 (1) and (IPr)Pd(acac)Cl (2) (IPr=(N,N′-bis(2,6- diisopropylphenyl)imidazol)-2-ylidene, acac=acetylacetonate) are described. Complex 2 can be prepared in a one-pot protocol in high yield. A study detailing the versatility of 2 to effectively catalyze a series of cross-coupling reactions is discussed.
