Jump to main content
Jump to site search

Issue 32, 2019
Previous Article Next Article

Ruthenium(ii)-catalysed selective C(sp2)–H bond benzoxylation of biologically appealing N-arylisoindolinones

Author affiliations

Abstract

Site- and regio-selective aromatic C–H bond benzoxylations were found to take place using biologically appealing N-arylisoindolinones under ruthenium(II) catalysis in the presence of (hetero)aromatic carboxylic acid derivatives as coupling partners. Besides the presence of two potential C(sp2)–H sites available for functionalization in the substrates, exclusive ortho selectivity was achieved in the phenyl ring attached to the nitrogen atom. Notably, the reactions occurred in a selective manner as only mono-functionalized products were formed and they tolerated a large number of functional chemical groups. The ability of the cyclic tertiary amide within the isoindolinone skeleton to act as a weak directing group in order to accommodate six-membered ring ruthenacycle intermediates appears to be the key to reach such high levels of selectivity. In contrast, the more sterically demanding cyclic imides were unreactive under identical reaction conditions.

Graphical abstract: Ruthenium(ii)-catalysed selective C(sp2)–H bond benzoxylation of biologically appealing N-arylisoindolinones

Back to tab navigation

Supplementary files

Publication details

The article was received on 14 May 2019, accepted on 22 Jul 2019 and first published on 23 Jul 2019


Article type: Paper
DOI: 10.1039/C9OB01122F
Org. Biomol. Chem., 2019,17, 7517-7525

  •   Request permissions

    Ruthenium(II)-catalysed selective C(sp2)–H bond benzoxylation of biologically appealing N-arylisoindolinones

    Y. Yuan, C. Bruneau, T. Roisnel and R. Gramage-Doria, Org. Biomol. Chem., 2019, 17, 7517
    DOI: 10.1039/C9OB01122F

Search articles by author

Spotlight

Advertisements