Ruthenium(ii)-catalysed selective C(sp)-H bond benzoxylation of biologically appealing N-arylisoindolinones
Résumé
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.
Domaines
Chimie
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Gramage-Doria_et al_2019_Ruthenium ii-catalysed selective C sp2_accepted.pdf (1.17 Mo)
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