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 Qumica, IST, 1049-001 Lisboa, Portugal, and REQUIMTE, Departamento de Qumica, FCT-UNL, 2829-516 Caparica, Portugal
J. Org. Chem., 2006, 71 (15), pp 5489–5497
DOI: 10.1021/jo060397a
Publication Date (Web): June 22, 2006
Copyright © 2006 American Chemical Society
†

 CQFM, Departamento de Engenharia Química.

,
‡

 REQUIMTE, Departamento de Química.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, carlosafonso@ist.utl.pt

Abstract

Abstract Image

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

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History

  • Published In Issue July 21, 2006
  • Received February 24, 2006

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