20912-50-9Relevant academic research and scientific papers
Oxidation of alcohols with nitroxyl radical resins under two-phase conditions
Kashiwagi, Yoshitomo,Ikezoe, Hiroshi,Ono, Tetsuya
, p. 69 - 72 (2006)
The oxidation of alcohols to carbonyl compounds such as aldehydes and ketones was studied using potassium hexacyanoferrate(III) mediated by nitroxyl radical polystyrene resins as catalyst under organic-aqueous two-phase conditions. Primary alcohols are readily oxidized to the corresponding aldehydes in excellent yield with no overoxidation to carboxylic acids. Secondary alcohols are converted to the corresponding ketones with a much lower efficiency. Oxidative cyclization of 1,4- and 1,5-diols to γ- and δ-lactones, respectively, proceeded nicely. Georg Thieme Verlag Stuttgart.
ASYMMETRIC INDUCTION IN BENZOIN BY PHOTOLYSIS OF BENZALDEHYDE ADSORBED IN CYCLODEXTRIN CAVITIES
Rao, Pushkara,Turro, Nicholas J.
, p. 4641 - 4644 (1989)
Irradiation of solid β-cyclodextrin complexes of benzaldehyde produces optically active benzoin as a major photo-product with an enantiomeric excess of up to 15percent.
Aromatization as an Impetus to Harness Ketones for Metallaphotoredox-Catalyzed Benzoylation/Benzylation of (Hetero)arenes
Lee, Shao-Chi,Li, Li-Yun,Tsai, Zong-Nan,Lee, Yi-Hsin,Tsao, Yong-Ting,Huang, Pin-Gong,Cheng, Cheng-Ku,Lin, Heng-Bo,Chen, Ting-Wei,Yang, Chung-Hsin,Chiu, Cheng-Chau,Liao, Hsuan-Hung
, p. 85 - 89 (2022/01/04)
Herein we report ketones as feedstock materials in radical cross-coupling reactions under Ni/photoredox dual catalysis. In this approach, simple condensation first converts ketones into prearomatic intermediates that then act as activated radical sources for cross-coupling with aryl halides. Our strategy enables the direct benzylation/benzoylation of (hetero)arenes under mild reaction conditions with high functional group tolerance.
Synthesis of biaryl ketones and biaryl diketones via carbonylative Suzuki-Miyaura coupling reactions catalyzed by bridged bis(N-heterocyclic carbene)palladium(II) catalysts
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Page/Page column 20; 25-30, (2021/12/23)
This disclosure relates to bridged bis(N-heterocyclic carbene)palladium(II) complexes, methods of preparing the complexes, and methods of using the complexes in Suzuki-Miyaura coupling reactions.
Self-Assembled 2,3-Dicyanopyrazino Phenanthrene Aggregates as a Visible-Light Photocatalyst
He, Min,Yu, Xiaoqiang,Wang, Yi,Li, Fei,Bao, Ming
, p. 5016 - 5025 (2021/04/12)
In this study, 2,3-dicyanopyrazino phenanthrene (DCPP), a commodity chemical that can be prepared at an industrial scale, was used as a photocatalyst in lieu of Ru or Ir complexes in C-X (X = C, N, and O) bond-forming reactions under visible-light irradiation. In these reactions, [DCPP]n aggregates were formed in situ through physical π-πstacking of DCPP monomers in organic solvents. These aggregates exhibited excellent photo- and electrochemical properties, including a visible light response (430 nm), long excited-state lifetime (19.3 μs), high excited-state reduction potential (Ered([DCPP]n*/[DCPP]n·-) = +2.10 V vs SCE), and good reduction stability. The applications of [DCPP]n aggregates as a versatile visible-light photocatalyst were demonstrated in decarboxylative C-C cross-coupling, amidation, and esterification reactions.
Palladium-Catalyzed Amide N-C Hiyama Cross-Coupling: Synthesis of Ketones
Idris, Muhammad Aliyu,Lee, Sunwoo
supporting information, p. 9190 - 9195 (2020/11/18)
N-Acylglutarimides and arylsiloxanes reacted in the presence of Pd(OAc)2/PCy3, Et3N·3HF, and LiOAc to provide the corresponding arylketones in good yields. Aryl-, vinyl-, and alkyl-substituted N-acylglutarimides showed good activity in the coupling reactions of arylsiloxanes. The reaction had a broad substrate scope and showed good functional group tolerance. N-Benzoylsuccinimide and N-protected N-phenylbenzamides showed good activities in coupling reactions with phenylsiloxane. The employment of CuF2 as an activor afforded the decarbonylative products at 160 °C.
Acyl radicals from α-keto acids using a carbonyl photocatalyst: Photoredox-catalyzed synthesis of ketones
Zhu, Da-Liang,Wu, Qi,Young, David James,Wang, Hao,Ren, Zhi-Gang,Li, Hong-Xi
supporting information, p. 6832 - 6837 (2020/10/12)
Acyl radicals have been generated from α-keto acids using inexpensive and commercially available 2-chloro-thioxanthen-9-one as the photoredox catalyst under visible light illumination. These reactive species added to olefins or coupled with aryl halides via a bipyridylstabilized Ni(II) catalyst, enabling easy access to a diverse range of ketones. This reliable, atom-economical, and eco-friendly protocol is compatible with a wide range of functional groups.
Imidazopyridine-fused [1,3]diazepinones: modulations of positions 2 to 4 and their impacts on the anti-melanoma activity
Ali, Lamiaa M. A.,Baccon-Sollier, Paul Le,Cuq, Pierre,Lichon, Laure,Malki, Yohan,Masurier, Nicolas,Maye, Morgane,Vincent, Laure-Ana?s
, p. 935 - 949 (2020/04/17)
A series of 19 novel pyrido-imidazodiazepinones, with modulations of positions 2, 3 and 4 of the diazepine ring were synthesised and screened for their in vitro cytotoxic activities against two melanoma cell lines (A375 and MDA-MB-435) and for their poten
Novel and efficient bridged bis(N-heterocyclic carbene)palladium(II) catalysts for selective carbonylative Suzuki–Miyaura coupling reactions to biaryl ketones and biaryl diketones
El Ali, Bassam,Fettouhi, Mohammed,Mansour, Waseem
, (2020/03/23)
Bridged N,N′-substituted bisbenzimidazolium bromide salts (L1, L2, and L3) were synthesized and fully characterized. Reactions of palladium acetate with L1, L2, and L3 afforded corresponding new bridged bis(N-heterocyclic carbene)palladium(II) complexes (C1, C2, and C3) in high yields. The X-ray structure of complex C1 showed that the Pd(II) ion is bonded to the two carbon atoms of the bis(N-heterocyclic carbene) and two bromido ligands are in the cis position, resulting in a distorted square planar geometry. The three Pd(NHC)2Br2 complexes C1, C2, and C3 were evaluated in carbonylative Suzuki–Miyaura coupling reactions of aryl boronic acids with aryl halides and displayed high catalytic activity with low catalyst loading. The coupling reactions of aryl bromides were selective towards the carbonylation product at higher carbon monoxide pressure.
N-Acyl-5,5-Dimethylhydantoins: Mild Acyl-Transfer Reagents for the Synthesis of Ketones Using Pd-PEPPSI or Pd/Phosphine Catalysts
Liu, Chengwei,Szostak, Michal,Wang, Chang-An
, p. 1043 - 1051 (2020/07/15)
N-Acyl-hydantoins have emerged as novel acyl-transfer reagents for the synthesis of ketones via selective N-C(O) cleavage. Herein, we report two new protocols for the cross-coupling of N-acyl-5,5-dimethylhydantoins using versatile and readily accessible Pd-PEPPSI or Pd/phosphine catalysts. The acyl Suzuki reactions afford biaryl ketones in good to excellent yields under operationally simple conditions using commercially available, bench- A nd air-stable twisted N-acyl-hydantoins as acyl donors. The method complements and expands on the previous protocol for the cross-coupling of N-acyl-hydantoins (Luo, Z.et al. Org. Process Res. Dev. 2018, 22, 1188).
