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Controllable construction of isoquinolinedione and isocoumarin scaffolds via RhIII-catalyzed C–H annulation of N-tosylbenzamides with diazo compounds

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Abstract

A highly efficient protocol for the synthesis of isoquinolinediones by RhIII-catalyzed C–H activation/annulation/decarboxylation of N-tosylbenzamides with diazo compounds is reported. The switchable synthesis of isocoumarins was also achieved successfully via C–H activation/annulation with slight modification of the reaction conditions. Importantly, the synthetic utility of this new reaction was further demonstrated in an atom-economical and operationally convenient total synthesis of a TDP2 inhibitor derivative from commercially available starting materials.

Graphical abstract: Controllable construction of isoquinolinedione and isocoumarin scaffolds via RhIII-catalyzed C–H annulation of N-tosylbenzamides with diazo compounds

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Publication details

The article was received on 14 Aug 2019, accepted on 10 Sep 2019 and first published on 10 Sep 2019


Article type: Paper
DOI: 10.1039/C9OB01789E
Org. Biomol. Chem., 2019, Advance Article

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    Controllable construction of isoquinolinedione and isocoumarin scaffolds via RhIII-catalyzed C–H annulation of N-tosylbenzamides with diazo compounds

    Y. Liu, J. Wu, B. Qian and Y. Shang, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01789E

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