103130-62-7Relevant academic research and scientific papers
Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates
Zhou, Yujing,Bandar, Jeffrey S.,Buchwald, Stephen L.
, p. 8126 - 8129 (2017)
The direct asymmetric copper hydride (CuH)-catalyzed coupling of α,β-unsaturated carboxylic acids to aryl alkenes to access chiral α-aryl dialkyl ketones is reported. A variety of substrate substitution patterns, sensitive functional groups, and heterocycles are tolerated in this reaction, which significantly expands the range of accessible products compared with existing hydroacylation methodology. Although mechanistic studies are ongoing, we propose that CuH-catalyzed silylation of unsaturated acids occurs to access a uniquely effective acyl electrophilic coupling partner.
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.
Photochemical Asymmetric Nickel-Catalyzed Acyl Cross-Coupling
Gandolfo, Eugenio,Tang, Xinjun,Raha Roy, Sudipta,Melchiorre, Paolo
, p. 16854 - 16858 (2019/11/11)
Photochemical enantioselective nickel-catalyzed cross-coupling reactions are difficult to implement. We report a visible-light-mediated strategy that successfully couples symmetrical anhydrides and 4-alkyl dihydropyridines (DHPs) to afford enantioenriched α-substituted ketones under mild conditions. The chemistry does not require exogenous photocatalysts. It is triggered by the direct excitation of DHPs, which act as a radical source and as a reductant, facilitating the turnover of the chiral catalytic nickel complex.
Two efficient pathways for the synthesis of aryl ketones catalyzed by phosphorus-free palladium catalysts
Wirwis,Feder-Kubis,Trzeciak
, p. 61 - 72 (2018/01/05)
Allylic alcohols, 1-buten-3-ol, 1-penten-3-ol and 1-octen-3-ol, reacted with aryl iodides (iodotoluene, 4-iodotoluene, 4-iodophenol and 4-iodanisole) under Heck reaction conditions to form corresponding saturated aryl ketones in one step. The same products were obtained in a two-step tandem reaction consisted of the Heck coupling of allylic alcohols with aryl iodides, followed by hydrogenation. Reactions were catalyzed by phosphorus-free palladium precursors modified with the menthol-substituted imidazolium chlorides. Formation of crystalline palladium nanoparticles, of the diameter up to 65 nm, in the reaction mixture was evidenced by TEM.
Chiral isoxazolidine-mediated stereoselective umpolung α-phenylation of methyl ketones
Takeda, Norihiko,Furuishi, Mizuki,Nishijima, Yuri,Futaki, Erika,Ueda, Masafumi,Shinada, Tetsuro,Miyata, Okiko
supporting information, p. 8940 - 8943 (2018/12/10)
An effective asymmetric α-phenylation of methyl ketones with triphenylaluminium in the presence of (+)-benzopyranoisoxazolidine has been developed. The reaction proceeds via the in situ formation of a chiral N-alkoxyenamine and the subsequent diastereoselective nucleophilic phenylation to provide α-phenylated products in moderate to good yields, with high enantioselectivities.
Iron-Catalyzed Methylation Using the Borrowing Hydrogen Approach
Polidano, Kurt,Allen, Benjamin D. W.,Williams, Jonathan M. J.,Morrill, Louis C.
, p. 6440 - 6445 (2018/07/25)
A general iron-catalyzed methylation has been developed using methanol as a C1 building block. This borrowing hydrogen approach employs a Kn?lker-type (cyclopentadienone)iron carbonyl complex as catalyst (2 mol %) and exhibits a broad reaction scope. A variety of ketones, indoles, oxindoles, amines, and sulfonamides undergo mono- or dimethylation in excellent isolated yields (>60 examples, 79% average yield).
SYNTHESIZING METHOD OF α-TERTIARY ARYL KETONE
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Paragraph 0099; 0102; 0103; 0104, (2017/08/02)
The present invention relates to a synthesizing method of alpha-tertiary aryl ketone. The synthesizing method of alpha-tertiary aryl ketone synthesizes alpha-tertiary aryl ketone by making aldehyde react with aryldiazoalkanes under a chiral boron Lewis ac
Enantioselective Oxidative Rearrangements with Chiral Hypervalent Iodine Reagents
Brown, Michael,Kumar, Ravi,Rehbein, Julia,Wirth, Thomas
supporting information, p. 4030 - 4035 (2016/03/16)
A stereoselective hypervalent iodine-promoted oxidative rearrangement of 1,1-disubstituted alkenes has been developed. This practically simple protocol provides access to enantioenriched α-arylated ketones without the use of transition metals from readily
Intermolecular Markovnikov-Selective Hydroacylation of Olefins Catalyzed by a Cationic Ruthenium-Hydride Complex
Kim, Junghwa,Yi, Chae S.
, p. 3336 - 3339 (2016/07/06)
The cationic Ru-H complex was found to be an effective catalyst for the intermolecular hydroacylation of aryl-substituted olefins with aldehydes to form branched ketone products. The preliminary kinetic and spectroscopic studies elucidated a ruthenium-acy
Catalytic Asymmetric Formal Insertion of Aryldiazoalkanes into the C-H Bond of Aldehydes: Synthesis of Enantioenriched Acyclic α-Tertiary Aryl Ketones
Kang, Byung Chul,Nam, Dong Guk,Hwang, Geum-Sook,Ryu, Do Hyun
supporting information, p. 4810 - 4813 (2015/10/12)
A novel, catalytic enantioselective route to synthesize a variety of α-tertiary aryl ketones via a boron Lewis acid promoted formal insertion of aryldiazoalkane into the C-H bond of both aromatic and aliphatic aldehydes is described. In the presence of ch
