53423-27-1Relevant academic research and scientific papers
N-heterocyclic carbene-palladium-imine complex catalyzed α-arylation of ketones with aryl and heteroaryl chlorides under air atmosphere
Lu, Hui-Yang,Shen, An,Li, Yong-Qing,Hu, Yu-Cai,Ni, Chen,Cao, Yu-Cai
supporting information, (2020/06/24)
A new structure of saturated ring skeleton monoligated NHC-Pd-Imine complex was easily synthesized and unambiguously confirmed by X-ray single crystal diffraction. It was found to be an efficient and air-stable catalyst for the α-arylation of ketones. The reaction could be operated in air without any negative effect. Non-activated aryl and heteroaryl chlorides have been successfully applied in the reaction with only 0.5 mol% catalyst loadings under air atmosphere. Excellent to good product yields were afforded.
Highly Ambiphilic Room Temperature Stable Six-Membered Cyclic (Alkyl)(amino)carbenes
Weinstein, Cory M.,Junor, Glen P.,Tolentino, Daniel R.,Jazzar, Rodolphe,Melaimi, Mohand,Bertrand, Guy
supporting information, p. 9255 - 9260 (2018/07/09)
Cyclic (alkyl)(amino)carbenes with a six-membered backbone were prepared. Compared to their five-membered analogues, they feature increased %Vbur and enhanced donor and acceptor properties, as evidenced by the observed n → π? transition trailin
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%).
Transition-Metal-Free α-Arylation of Enolizable Aryl Ketones and Mechanistic Evidence for a Radical Process
Pichette Drapeau, Martin,Fabre, Indira,Grimaud, Laurence,Ciofini, Ilaria,Ollevier, Thierry,Taillefer, Marc
supporting information, p. 10587 - 10591 (2015/09/02)
The α-arylation of enolizable aryl ketones can be carried out with aryl halides under transition-metal-free conditions using KOtBu in DMF. The α-aryl ketones thus obtained can be used for step- and cost-economic syntheses of fused heterocycles and Tamoxifen. Mechanistic studies demonstrate the synergetic role of base and solvent for the initiation of the radical process.
Di-tert-butylneopentylphosphine (DTBNpP): An Efficient Ligand in the Palladium-Catalyzed α-Arylation of Ketones
Raders, Steven M.,Jones, Jessica M.,Semmes, Jeffrey G.,Kelley, Steven P.,Rogers, Robin D.,Shaughnessy, Kevin H.
, p. 7395 - 7404 (2016/02/19)
Di-tert-butylneopentylphosphine (DTBNpP) and palladium(II) acetate provide an efficient catalytic system for the α-arylation of ketones. Aryl bromides were coupled with ketones using 0.25-0.5 mol-% Pd(OAc)2/DTBNpP in toluene at 50 C, whereas aryl chlorides required a higher catalyst loading (0.5-2.0 mol-%) and a higher temperature (80 C). Coupling of 2-bromophenol with ketones using the Pd/DTBNpP system provides an efficient route for the synthesis of benzofurans.
From acetone metalation to the catalytic α-arylation of acyclic ketones with NHC-nickel(II) complexes
Henrion, Mickael,Chetcuti, Michael J.,Ritleng, Vincent
supporting information, p. 4624 - 4627 (2014/05/06)
Air-stable N-heterocyclic carbene-nickel(II) complexes at concentrations as low as 1 mol% exhibit high catalytic activity for the α-arylation of acyclic ketones and join a highly restricted list of nickel catalysts for this key reaction. Mechanistic investigations suggest a radical pathway. the Partner Organisations 2014.
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-palladium(II)-1-methylimidazole complex catalyzed α-arylation of ketones with aryl chlorides
Xiao, Zheng-Kang,Shao, Li-Xiong
experimental part, p. 711 - 716 (2012/04/04)
An easily available NHC-Pd(II)-Im (NHC=N-heterocyclic carbene, Im=1-methylimidazole) complex was found to be an efficient catalyst for the α-arylation reaction between ketones and aryl chlorides. Under the optimal conditions, all reactions proceeded smoot
(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)
Chiral bronsted acid from a cationic gold(I) complex: Catalytic enantioselective protonation of silyl enol ethers of ketones
Cheon, Cheol Hong,Kanno, Osamu,Toste, F. Dean
supporting information; experimental part, p. 13248 - 13251 (2011/10/10)
A chiral Bronsted acid has been developed from a cationic gold(I) disphosphine complex in the presence of alcoholic solvent and applied to the enantioselective protonation reaction of silyl enol ethers of ketones. Various optically active cyclic ketones were obtained in excellent yields and high enantioselectivities, including cyclic ketones bearing aliphatic substrates at the α-position. Furthermore, the application of this Bronsted acid was extended to the first Bronsted acid-catalyzed enantioselective protonation reaction of silyl enol ethers of acyclic substrates, regardless of their E/Z ratio.
