Jump to main content
Jump to site search

Issue 102, 2015
Previous Article Next Article

Copper-catalysed cross-coupling affected by the Smiles rearrangement: a new chapter on diversifying the synthesis of chiral fluorinated 1,4-benzoxazine derivatives

Author affiliations

Abstract

Synthesis of different chiral fluorinated Boc-[1,4]benzoxazins from their open chain precursors were investigated. The NMR spectra and crystallographic data showed the presence of the Smiles Rearrangement (SR) followed by copper catalysed coupling. The influence of the Boc protecting group, solvent, base, catalyst and the conformational changes of adducts was explored in detail by careful reaction optimization. No product was obtained in the absence of Boc, indicating its crucial role. Finally, a new mechanism for the SR copper catalysed ring closure was proposed.

Graphical abstract: Copper-catalysed cross-coupling affected by the Smiles rearrangement: a new chapter on diversifying the synthesis of chiral fluorinated 1,4-benzoxazine derivatives

Back to tab navigation

Supplementary files

Publication details

The article was received on 14 Sep 2015, accepted on 25 Sep 2015 and first published on 28 Sep 2015


Article type: Communication
DOI: 10.1039/C5RA18897K
Author version
available:
Download author version (PDF)
RSC Adv., 2015,5, 83576-83580

  •   Request permissions

    Copper-catalysed cross-coupling affected by the Smiles rearrangement: a new chapter on diversifying the synthesis of chiral fluorinated 1,4-benzoxazine derivatives

    S. Alapour, D. Ramjugernath and N. A. Koorbanally, RSC Adv., 2015, 5, 83576
    DOI: 10.1039/C5RA18897K

Search articles by author

Spotlight

Advertisements