Literature DB >> 24967946

One-pot, two-step desymmetrization of symmetrical benzils catalyzed by the methylsulfinyl (dimsyl) anion.

Daniele Ragno1, Olga Bortolini, Pier Paolo Giovannini, Alessandro Massi, Salvatore Pacifico, Anna Zaghi.   

Abstract

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.

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Year:  2014        PMID: 24967946     DOI: 10.1039/c4ob00759j

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  1 in total

1.  Electron-transfer-initiated benzoin- and Stetter-like reactions in packed-bed reactors for process intensification.

Authors:  Anna Zaghi; Daniele Ragno; Graziano Di Carmine; Carmela De Risi; Olga Bortolini; Pier Paolo Giovannini; Giancarlo Fantin; Alessandro Massi
Journal:  Beilstein J Org Chem       Date:  2016-12-13       Impact factor: 2.883

  1 in total

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