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Rh(II)-Catalyzed Intramolecular C-H Insertion of Diazo Substrates in Water: Scope and Limitations

Nuno R. Candeias, Pedro M. P. Gois and Carlos A. M. Afonso*

*CQFM, Departamento de Engenharia Química, IST, 1049-001 Lisboa, Portugal, and REQUIMTE, Departamento de Química, FCT-UNL, 2829-516 Caparica, Portugal, Email:

N. R. Candeias, P. M. P. Gois, C. A. M. Afonso, J. Org. Chem., 2006, 71, 5489-5497.

DOI: 10.1021/jo060397a

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Preferential Rh(II) carbenoid intramolecular C-H versus O-H insertion derived from α-diazo-acetamides can be achieved in water by creating a large hydrophobic environment around the reactive carbenoid center using an appropriate combination of the catalyst and amide groups.

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ID: J42-Y2006-2070