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Taylor and Francis Group, Green Chemistry Letters and Reviews, 2(5), p. 211-240, 2012

DOI: 10.1080/17518253.2011.620009

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Intramolecular C–H insertion catalyzed by dirhodium(II) complexes using CO2as the reaction media

Journal article published in 2012 by Małgorzata E. Zakrzewska, Pedro M. S. D. Cal, Nuno R. Candeias ORCID, Rafał Bogel-Łukasik, Carlos A. M. Afonso, Manuel N. Ponte, Pedro M. P. Gois ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

In this work, the intramolecular C-H insertion of diazoacetamides catalyzed by dirhodium(II) complexes and using CO2 as solvent is disclosed. The expected lactams were obtained in yields over 97%. The asymmetric intramolecular C-H insertion was also achieved and the beta-lactam 14 was obtained in > 97% yield and 65% ee using the chiral dirhodium(II) catalyst Rh-2(S-PTTL)(4). Finally, the dirhodium(II) complex Rh-2(OAc)(4) was used in two consecutive cycles in which complete conversion to the lactam was observed.