- 9-(Diphenylphosphino)anthracene-based phosphapalladacycle catalyzed conjugate addition of arylboronic acids to electron-deficient alkenes
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9-(Diphenylphosphino)anthracene-based phosphapalladacycle catalyzed conjugate addition of arylboronic acids to electron-deficient alkenes such asα,β-unsaturated ketones, esters, nitrile and nitroalkenes gave corresponding β-arylated alkanes in good yields and achieved TON up to 700.
- Shimizu, Minori,Yamamoto, Tetsuya
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supporting information
(2020/08/06)
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- Palladium-catalyzed redox cascade for direct β-arylation of ketones
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Herein we report a full article about the detailed design and development of two palladium-catalyzed redox cascade methods that enable direct β-arylation of ketones. Palladium-catalyzed ketone dehydrogenation, aryl-X bond activation and conjugate addition were merged into a redox-neutral catalytic cycle. Non-metal-based aryl electrophiles were used as both the oxidant and the aryl source. The β-arylation with aryl iodides was achieved site-selectively with Pd(TFA)2/P(i-Pr)3 as the precatalyst and AgTFA as the iodide scavenger. Both cyclic and linear ketones can react to give β-aryl ketones with excellent functional group tolerance. The β-arylation with diaryliodonium salts was realized without stoichiometric heavy metal additives, and proved to be redox-neutral. A wider substrate scope regarding aryl groups and ketones was obtained for the arylation with diaryliodonium salts, and the possible involvement of palladium nanoparticles as the active catalyst was examined and discussed.
- Huang, Zhongxing,Dong, Guangbin
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supporting information
p. 3253 - 3265
(2018/05/04)
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- Palladium-Catalyzed Direct β-C?H Arylation of Ketones with Arylboronic Acids in Water
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A palladium-catalyzed direct β-C?H arylation of ketones was developed under mild conditions in water, featuring commercially available arylboronic acids as nucleophilic aryl sources and o-iodoxybenzoic acid as the oxidant. The method provides a concise route to access β-arylated ketones. Preliminary studies indicated that direct asymmetric β-C?H arylation of ketones could be achieved by this strategy. (Figure presented.).
- Hu, Xiaoyun,Yang, Xiaobo,Dai, Xi-Jie,Li, Chao-Jun
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supporting information
p. 2402 - 2406
(2017/07/22)
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- Pd NPs-Loaded Homochiral Covalent Organic Framework for Heterogeneous Asymmetric Catalysis
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We herein report the fabrication of a palladium nanoparticles (Pd NPs) loaded homochiral covalent organic framework using S-(+)-2-methylpiperazine and cyanuric chloride (Pd@CCOF-MPC) (2) via a very facile chemical approach. The chiral COF support of 1 (CC
- Ma, Hui-Chao,Kan, Jing-Lan,Chen, Gong-Jun,Chen, Cheng-Xia,Dong, Yu-Bin
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p. 6518 - 6524
(2017/08/18)
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- DIRECT B-ARYLATION OF CARBONYL COMPOUNDS
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Disclosed is a method for the β-C—H H functionalization of carbonyl compounds that is both selective and broadly applicable. The methods provide direct β-arylation of carbonyl compound with a diverse array of aryl or heteroaryl halides, aryl or heteroryl tosylate, aryl or heteroaryl triflates, or diaryliodonium salts, by palladium catalysis in the presence of a ligand and promoter.
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Paragraph 0123-0125; 128
(2016/09/12)
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- Palladium-catalyzed direct β-arylation of ketones with diaryliodonium salts: A stoichiometric heavy metal-free and user-friendly approach
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We herein report a new protocol for the Pd-catalyzed β-arylation of ketones without stoichiometric heavy metals. Widely accessible diaryliodonium salts are used as both the oxidant and aryl source. This tandem redox catalysis merges ketone dehydrogenation and conjugate addition without an additional oxidant or reductant. This transformation features the use of a unique bis-N-tosylsulfilimine ligand and the combination of potassium trifluoroacetate/trifluoroacetic acid to maintain an appropriate acidity of the reaction medium. The reaction tolerates both air and moisture, and shows a broad substrate scope. Kinetics studies, along with filtration and poisoning tests, support the involvement of palladium nanoparticles in the catalysis.
- Huang, Zhongxing,Sam, Quynh P.,Dong, Guangbin
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p. 5491 - 5498
(2015/09/28)
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- Catalytic direct β-arylation of simple ketones with aryl iodides
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Herein we report a direct β-arylation of simple ketones with widely available aryl iodides, combining palladium-catalyzed ketone oxidation, aryl-halide activation, and conjugate addition through a single catalytic cycle. Simple cyclic ketones with different ring-sizes, as well as acyclic ketones, can be directly arylated at the β-position with complete site-selectivity and excellent functional group tolerance.
- Huang, Zhongxing,Dong, Guangbin
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p. 17747 - 17750
(2014/01/06)
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- Co-ligand effects in the catalytic activity of Pd(II)-NHC complexes
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Three cis-chelating di-N-heterocyclic carbene palladium(II) complexes [PdX2(diNHC)] (X = I, 1; X = SCN, 2; X = CF3CO 2, 3) bearing different anionic co-ligands were synthesized and fully characterized. A comparison of thei
- Yeung, Andrew Dahao,Ng, Pearly Shuyi,Huynh, Han Vinh
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experimental part
p. 112 - 117
(2011/02/17)
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