4.8 Article

Rh(III)-Catalyzed C-H Activation/Cyclization of Benzamides and Diazonaphthalen-2(1H)-ones for Synthesis of Lactones

Journal

ORGANIC LETTERS
Volume 19, Issue 15, Pages 4002-4005

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01728

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Funding

  1. National Natural Science Foundation of China [21472163]

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A Rh(III)-catalyzed C-H activation/cyclization of benzamides and diazonaphthalen-2(1H)-ones for synthesis of lactones has been developed. In the presence of Rh(III) catalysis, the benzamides would form rhodacycle species and could be trapped by diazonaphthalen-2(1H)-ones for arylation, and the following intramolecular lactonization would rapidly furnish the products.. Thus, the diazonaphthalen-2(1H)-ones were first revealed as a lactonization component in Rh(III)-catalysis, while the kinetic isotope effect study was conducted and a plausible reaction mechanism was proposed.

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