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Issue 32, 2019
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Ruthenium(ii)-catalysed selective C(sp2)–H bond benzoxylation of biologically appealing N-arylisoindolinones

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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

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Supplementary files

Article information


Submitted
14 May 2019
Accepted
22 Jul 2019
First published
23 Jul 2019

Org. Biomol. Chem., 2019,17, 7517-7525
Article type
Paper

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

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