42797-68-2Relevant academic research and scientific papers
Design of an Indolylphosphine Ligand for Reductive Elimination-Demanding Monoarylation of Acetone Using Aryl Chlorides
Fu, Wai Chung,So, Chau Ming,Chow, Wing Kin,Yuen, On Ying,Kwong, Fuk Yee
supporting information, p. 4612 - 4615 (2015/09/28)
The rational design of a phosphine ligand for the reductive elimination-demanding Pd-catalyzed mono-α-arylation of acetone is demonstrated and reported. The catalyst is tolerant of previously proven challenging electron-deficient aryl chlorides and provides excellent product yields with down to 0.1 mol % Pd. Preliminary investigations suggest that the rate-limiting step for the proposed system is the oxidative addition of aryl chlorides, in which it contradicts previous findings regarding the α-arylation of acetone with aryl halides.
Palladium-catalyzed mono-α-arylation of acetone with aryl imidazolylsulfonates
Ackermann, Lutz,Mehta, Vaibhav P.
supporting information; experimental part, p. 10230 - 10233 (2012/09/22)
Set the ace(tone): A palladium catalyst derived from the bidentate XantPhos ligand and Pd(OAc)2 has enabled broadly applicable mono-α-arylations of acetone to be performed with air- and moisture-stable aryl imidazolylsulfonates as most user-friendly electrophiles (see scheme). Copyright
Palladium-catalyzed mono-α-arylation of acetone with aryl halides and tosylates
Hesp, Kevin D.,Lundgren, Rylan J.,Stradiotto, Mark
supporting information; experimental part, p. 5194 - 5197 (2011/06/10)
We report the first example of selective Pd-catalyzed mono-α- arylation of acetone employing aryl chlorides, bromides, iodides, and tosylates. The use of appropriately designed P,N-ligands proved to be the key to controlling the reactivity and selectivity. The reaction affords good yields with substrates containing a range of functional groups at modest Pd loadings using Cs2CO3 as the base and employing acetone as both a reagent and the solvent.(Figure Presented)
Behaviour of Arylazo tert-Butyl Sulfides with Ketone Enolates. Competition between SRN1 α-Arylation and Azocoupling Reactions.
Dell'Erba, Carlo,Novi, Marino,Petrillo, Giovanni,Tavani, Cinzia
, p. 325 - 334 (2007/10/02)
(Z)-Arylazo tert-butyl sulfides 1a-i react, in DMSO and at room temperature, with potassium acetone enolate to give good yields of 1-aryl-2-propanones via spontaneous SRN1 dark reactions. α-Phenylation of pincolone and acetophenone enolates by 1a likewise occurs in excellent yields.In agreement with the involvement of an electron-transfer catalyzed chain process, the reaction of the 4-bromo derivative 1n with pinacolone enolate gives mainly the bis-substitution product 13.With azosulfides 1j-m the arylation pathway competes with a base-induced thiol elimination eventually leading, depending on the structure of the azosulfide, to indazoles 8 or 11 and/or to 2-oxopropanal arylhydrazones 9, 10 or 12.
Arylation and 1-Alkenylation on α-Position of Ketones via Tributyltin Enolates Catalyzed by Palladium Complex
Kosugi, Masanori,Hagiwara, Isao,Sumiya, Takao,Migita, Toshihiko
, p. 241 - 246 (2007/10/02)
The reaction of tributyltin enolates, prepared from tributyltin methoxide and enol acetates in situ, with aryl and 1-alkenyl bromides in the presence of dichlorobis(tri-o-tolylphosphine)palladium was found to give α-aryl and α-(1-alkenyl) ketones, respectively, in good yields with essentially complete retention of the enol acetate regiochemistry.
Azomethines, 1-Azaallyl Anions, and Metastable Secondary Enamines
Knorr, Rudolf,Weiss, Alfons,Loew, Peter,Raepple, Edith
, p. 2462 - 2489 (2007/10/02)
E/Z equilibrium constants of the ketone anils 6a-s do not depend significantly on the inductive substituent effect. 1H NMR chemical shifts used for configurational classification are also effective for assignments in comparable, isomerically almost pure azomethines 6aa-pp and may be explained by the anisotropic shift model.The 1-azaallyl anions 7 prepared by deprotonation are characterized by 1H NMR spectroscopy.Kinetic and thermodynamic control of this metallation reaction result in different preferential configurations of such anions, the methanolysis of which yields metastable sec. enamines 8 by regio- and stereospecific N-protonation.It is possible to estimate further substituent parameters λd from E/Z equilibria.
