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The regioselectivity of copper(i)-catalyzed synthesis of 1,2,3-triazoles in dabco-based ionic liquids has been investigated at the DFT level using a supermolecular approach. The analysis of the theoretical results shows that the coordination ability of the ionic liquid (IL) anion to copper(i) catalyst and to all the other species containing the copper (intermediates and transition states) can significantly affect product distribution. Possible catalyst sequestering effects and the ability to stabilize selectively new intermediate species have been envisaged, as probable mechanisms throughout IL anions can affect copper catalyzed reactions inside performed. © 2010 the Owner Societies.

Ragno D.,Laboratorio Of Chimica Organica | Bortolini O.,Laboratorio Of Chimica Organica | Giovannini P.P.,Laboratorio Of Chimica Organica | Massi A.,Laboratorio Of Chimica Organica | And 2 more authors.
Organic and Biomolecular Chemistry | Year: 2014

An operationally simple one-pot, two-step procedure for the desymmetrization of benzils is herein described. This consists in the chemoselective cross-benzoin reaction of symmetrical benzils with aromatic aldehydes catalyzed by the methyl sulfinyl (dimsyl) anion, followed by microwave-assisted oxidation of the resulting benzoylated benzoins with nitrate, avoiding the costly isolation procedure. Both electron-withdrawing and electron-donating substituents may be accommodated on the aromatic rings of the final unsymmetrical benzil. © the Partner Organisations 2014.

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