56705-50-1

Upstream product

• 90-90-4 (4-bromophenyl)(phenyl)methanone 
• 93-55-0 1-phenyl-propan-1-one 
• 134-85-0 4-chlorobenzophenone 
• 98-56-6 4-chlorobenzotrifluoride 

Relevant academic research and scientific papers

Nickel catalyzed α-arylation of ketones with aryltrimethylammonium triflates

Nickel-catalyzed α-arylation of ketones involving aromatic C-N cleavage has been accomplished. Intermolecular coupling of aromatic ketones with a variety of aryltrimethylammonium triflates was achieved in the presence of Ni(COD)2, IPr·HCl, and LiOBut, giving α-arylated ketones in reasonable to excellent yields.

Nickel-Catalyzed Transformation of Aryl 2-Pyridyl Ethers via Cleavage of the Carbon-Oxygen Bond: Synthesis of Mono-α-arylated Ketones

The nickel/IPr-catalyzed reaction of aryl 2-pyridyl ethers with propiophenone and acetophenone derivatives via C-OPy bond cleavage is performed in the presence of t -BuOLi to give mono-α-arylated ketones in moderate yields. The method is suitable for electron-rich and electron-poor ethers as well as heteroaryl ethers and tolerates a range of active functional groups.

Palladium-catalyzed α-arylation of arylketones at low catalyst loadings

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

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.

Nickel-NHC-catalyzed α-arylation of acyclic ketones and amination of haloarenes and unexpected preferential N-arylation of 4-aminopropiophenone

(Chemical Equation Presented) Arylation of both acyclic ketones and primary and secondary amines was achieved using a new, simple, stable, and easy-to-access nickel(II)-halide complex bearing mixed PPh3/N- heterocyclic carbene ligands as a catalyst precursor. Acyclic ketones were first arylated at the α-position with the nickel catalyst. On the other hand, less basic amines, such as diphenylamine and 4-aminobenzophenone, were more favorable in the catalytic amination of haloarenes than basic amines, contrary to previous reports. N-Arylation of 4-aminopropiophenone was found to proceed selectively without causing α-arylation of the ketone group.

Well-defined, air-stable (NHC)Pd(Allyl)Cl (NHC = N-heterocyclic carbene) catalysts for the arylation of ketones

(formula presented) A number of palladium-N-heterocyclic carbene (NHC) complexes were found to be active catalysts for the arylation of ketones. A large number of substrates, both aryl halides and ketones, are compatible with the reaction conditions. The ketone arylation reactions are achieved with low catalyst loading in short reaction times using aryl chlorides and triflates as reactive partners.

Simple, highly active palladium catalysts for ketone and malonate arylation: Dissecting the importance of chelation and steric hindrance

A remarkably active catalyst system for α-arylation of ketones and malonates was developed by proposing that sterically hindered alkylphosphines would accelerate the catalytic reaction rates. We initially tested the bisphosphine ligand D'BPF (1,1'-bis-(di-tert-butylphosphino)ferrocene) for this palladium-catalyzed chemistry. This catalyst system led to fast reaction rates for reactions of aryl bromides with ketones, including room temperature chemistry in many cases. In some cases turnover numbers were 20 000. The catalyst also gave mild reactions with aryl chlorides with yields that were similar to the chemistry with aryl bromides. Independent synthesis of the arylpalladium enolate complexes with isobutyrophenone enolate showed that only one phosphorus of the bisphosphine ligand D'BPF was coordinated in the enolate complex. Thus, we tested sterically hindered alkylphosphine ligands for the ketone and malonate arylation process and found that P(t-Bu)3 gave exceptionally fast rates and high turnover numbers for these reactions. These results demonstrate several principles for the catalytic chemistry that we did not anticipate: palladium complexes of monophosphine ligands can activate aryl chlorides under mild conditions, and palladium enolates coordinated by certain monophosphines can undergo C-C bond-forming reductive elimination much faster than β-hydrogen elimination.