 |
 |
 |
Journal articles
Ruthenium(ii)-catalysed selective C(sp)-H bond benzoxylation of biologically appealing N-arylisoindolinones
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(sp 2)-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-memberd 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 idential reaction conditions.
Cited literature [47 references]
https://hal-univ-rennes1.archives-ouvertes.fr/hal-02280834
Contributor : Laurent Jonchère <>
Submitted on : Tuesday, December 3, 2019 - 3:20:16 PM
Last modification on : Wednesday, January 13, 2021 - 3:08:02 AM
Long-term archiving on: : Wednesday, March 4, 2020 - 5:56:09 PM
Contributor : Laurent Jonchère <>
Submitted on : Tuesday, December 3, 2019 - 3:20:16 PM
Last modification on : Wednesday, January 13, 2021 - 3:08:02 AM
Long-term archiving on: : Wednesday, March 4, 2020 - 5:56:09 PM
File
Gramage-Doria_et al_2019_Ruthe...
Files produced by the author(s)