Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Rh(III)-Catalyzed C–H Cyclization of Arylnitrones with Diazo Compounds: Access to 3-Carboxylate Substituted N-Hydroxyindoles

Rh(III)-Catalyzed C–H Cyclization of Arylnitrones with Diazo Compounds: Access to 3-Carboxylate Substituted N-Hydroxyindoles
Jian Li, Xiaowei Wu, Hong Liu, Yazhou Li, Yu Zhou
Recently, N-hydroxyindole derivatives have received much interest because of their unique structural motif and various biological activities. In this study, we report the first example of a Rh(III)-catalyzed reaction of arylnitrones with α-diazoketoesters or α-diazodiketones to produce N-hydroxyindole derivatives. Intriguingly, we could build the N-hydroxyindole scaffold by blocking the cleavage of the N–O bond selectively, while eliminating the acyl group of α-diazoketoesters or α-diazodiketones preferentially.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01393

DOI: 10.1021/acs.joc.7b01393

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