- Metal Free, Direct and Selective Deoxygenation of α-Hydroxy Carbonyl Compounds: Access to α,α-Diaryl Carbonyl Compounds
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An efficient, metal free, direct and selective deoxygenation of α-hydroxy carbonyl compounds is achieved with the aid of catalytic amount of aqueous HClO4 (70 %) and triethylsilane as hydride source. A variety of α-hydroxy-α,α-diaryl carbonyl compounds are selectively deoxygenated to give α,α-diaryl carbonyl compounds in good to excellent yields. Intermediacy of α-keto carbenium ion is proposed on the basis of some control experiments and atmospheric pressure chemical ionization mass spectral analysis.
- Kumar, Anil,Sandeep,Venugopalan, Paloth
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- Aqueous α-Arylation of Mono- and Diarylethanone Enolates at Low Catalyst Loading
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Acetophenone and deoxybenzoin derivatives are selectively α-arylated using a combination of very small amounts of palladium acetate and diphenylphosphine oxide as catalyst system and water as the only solvent. Target di- and triarylethanones are isolated virtually free of metal residues, and the reaction is amenable to gram-scale. A mechanistic proposal based on TEM images, poisoning experiments, kinetic plot and ESI-MS spectrometry is also provided. (Figure presented.).
- Astarloa, Iratxe,SanMartin, Raul,Herrero, María Teresa,Domínguez, Esther
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supporting information
p. 1711 - 1718
(2018/03/21)
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- Regioselective Arylation Reactions of Biphenyl-2-ols, Naphthols, and Benzylic Compounds with Aryl Halides under Palladium Catalysis
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Biphenyl-2-ols undergo regioselective mono- and diarylation upon a treatment with aryl iodides in the presence of a palladium catalyst in DMF using Cs2CO3 as a base to produce 1,1′ : 2′,1″-terphenyl-2-ol and 2′,6′-diphenylbiphenyl-2-ol and their derivatives. The reaction of 1-naphthol selectively occurs at its 8-position to give 8-aryl-1-naphthols. In the reaction of 2-naphthol with aryl bromides, diarylated compounds, 1-(2-arylphenyl)-2-naphthols, are formed as the single major products. Under similar conditions, benzyl ketones, phenylacetonitrile, and methyl phenylacetate are arylated at their benzylic position.
- Satoh, Tetsuya,Inoh, Jun-Ichi,Kawamura, Yoshiki,Kawamura, Yuichiro,Miura, Masahiro,Nomura, Masakatsu
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p. 2239 - 2246
(2007/10/03)
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