Organic Letters
Organic Letters
5 years ago

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

Rh(III)-Catalyzed C–H Activation/Cyclization of Benzamides and Diazonaphthalen-2(1H)-ones for Synthesis of Lactones
Sunliang Cui, Renjie Chen
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01728

DOI: 10.1021/acs.orglett.7b01728

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