- Desulfurization of dibenzothiophene and dibenzothiophene sulfone via Suzuki–Miyaura type reaction: Direct access to o-terphenyls and polyphenyl derivatives
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The reactivity of dibenzothiophene (DBT) or dibenzothiophene sulfone (DBTO2) with a variety of phenylboronic acids was mediated by the nickel precursor [Ni(dippe)Cl2] in the presence of a base. The reaction was performed under relatively mild conditions (70–100 °C), in aqueous media. The study of the reactivity revealed the role of water as a hydrogen source and showed a competition between the desulfurization of the corresponding substrates via a hydrodesulfurization (HDS) or by a hydrodesulfurative cross-coupling (HDSCC) reaction. Furthermore, in the absence of water sulfur-free poly-phenylic compounds were obtained in good yields as a result of a Suzuki–Miyaura type reaction, being the main product in most of the cases the corresponding o-terphenyl derivative, these products are valuable building blocks in the synthesis of more complex materials.
- Gutiérrez-Ordaz, Rubén,García, Juventino J.
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p. 373 - 381
(2018/08/31)
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- Ir-catalyzed synthesis of substituted tribenzosilepins by dehydrogenative C-H/Si-H coupling
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The Ir-catalyzed intramolecular reaction of 2′,6′-diaryl-2-(hydrosilyl)biphenyls gave substituted tribenzosilepins by direct dehydrogenative C-H/Si-H coupling. This is the first example of catalytic construction of the tribenzosilepin skeleton. Enantiomer
- Shibata, Takanori,Uno, Ninna,Sasaki, Tomoya,Takano, Hideaki,Sato, Tatsuki,Kanyiva, Kyalo Stephen
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p. 3426 - 3432
(2018/04/14)
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- Photochemical reactions of 1,3,3-trimethylbicyclo[2.2.2]octa-5,7-dien-2- ones
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The photochemistry of 1,3,3-trimethylbicyclo[2.2.2]octa-5,7-dien-2-ones 1a-f containing multiple chromophoric moieties under various conditions is described. Upon direct irradiation, dienones 1a-f in benzene, acetonitrile, and methanol were found to aromatize through photoelimination of dimethylketene, which was trapped with 3-phenylprop-2-en-1-ol (12). Triplet sensitization of dienone 1a in acetone and in acetone/acetophenone mixed solvents afforded aromatic compound 2a, whilst bicyclic systems 1b-c were found to be unreactive on sensitization. In the cases of dienones 1d-f in acetone, aromatic compounds 2d-f and di-π-methane (DPM) photoproducts 3d-f and 4f were observed, but in the acetone/acetophenone mixed solvent system only DPM photoproducts were detected. Plausible mechanisms for these photochemical reactions are described. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Chang, Shi-Yi,Huang, Shih-Lin,Villarante, Nelson R.,Liao, Chun-Chen
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p. 4648 - 4657
(2007/10/03)
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