64977-33-9Relevant 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.
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.
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.
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.
A highly active and selective palladium pincer catalyst for the formation of α-aryl ketones via cross-coupling
Bugarin, Alejandro,Connell, Brian T.
supporting information; experimental part, p. 7218 - 7220 (2011/08/09)
Several air and moisture stable Pd(ii) pincer complexes were synthesized via oxidative addition of Pd(0) to novel PheBox pincer ligand precursors. Low loadings (1 mol%) of the Pd complex [t-BuPhebox-Me2]PdBr are capable of efficiently promoting the selective α-monoarylation of a variety of ketones with numerous aryl bromides in only 1 h at 70°C with 82-99% yields.
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.
(IPr)Pd(acac)Cl: An easily synthesized, efficient, and versatile precatalyst for C-N and C-C bond formation
Marion, Nicolas,Ecarnot, Elise C.,Navarro, Oscar,Amoroso, Dino,Bell, Andrew,Nolan, Steven P.
, p. 3816 - 3821 (2007/10/03)
A very straightforward synthesis of (IPr)Pd(acac)Cl from two commercially available starting materials, Pd(acac)2 and IPr·HCl [acac = acetylacetonate; IPr = N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], has been developed. The resulting complex, (IPr)Pd(acac)Cl (1), has proven to be a highly active PdII precatalyst in the Buchwald-Hartwig and the α-ketone arylation reactions. A wide range of substrates has been screened, including unactivated, sterically hindered, and heterocyclic aryl chlorides.
NUCLEOPHILIC HETEROCYCLIC CARBENE DERIVATIVES OF PD(ACAC)2 FOR CROSS-COUPLING REACTIONS
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Page/Page column 21, 41-42, 46, (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.
An efficient and mild protocol for the α-arylation of ketones mediated by an (imidazol-2-ylidene)palladium(acetate) system
Singh, Rohit,Nolan, Steven P.
, p. 5832 - 5840 (2007/10/03)
The activity of well-defined N-heterocyclic carbene (NHC)-palladium acetate complexes has been studied in the α-arylation of ketones. The enolate was generated in situ via use of slight excess of sodium tert-butoxide as base. The results showed a high act
Relative Migratory Aptitudes of Doubly and Triply Bonded Groups in a Cycloheptatriene System
Battye, Peter J.,Jones, David W.
, p. 1479 - 1490 (2007/10/02)
In cyclopentadiene systems, 1,5-shift of triply bonded groups is much slower than that of doubly bonded groups, whereas in the cycloheptatriene systems (34) and (29), as well as in (21) and (19), CN and CHO groups have very similar migratory tendencies.In
