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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.
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Submitted on : Tuesday, December 3, 2019 - 3:20:16 PM
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Yu-Chao Yuan, Christian Bruneau, Thierry Roisnel, Rafael Gramage-Doria. Ruthenium(ii)-catalysed selective C(sp)-H bond benzoxylation of biologically appealing N-arylisoindolinones. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2019, 17 (32), pp.7517-7525. ⟨10.1039/c9ob01122f⟩. ⟨hal-02280834⟩



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