Synthesis 2012; 44(14): 2173-2180
DOI: 10.1055/s-0031-1291048
special topic
© Georg Thieme Verlag Stuttgart · New York

Internal Lewis Acid Assisted Benzoic Acid Catalysis

Autoren

  • Tyler J. Auvil

    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA, Fax: +1(614)2921685   eMail: mattson@chemistry.ohio-state.edu
  • Anita E. Mattson*

    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA, Fax: +1(614)2921685   eMail: mattson@chemistry.ohio-state.edu
Weitere Informationen

Publikationsverlauf

Received: 09. März 2012

Accepted: 22. März 2012

Publikationsdatum:
25. Mai 2012 (online)


Graphical Abstract

Abstract

Internal Lewis acid assisted benzoic acid derivatives are introduced as new low-molecular-weight single-hydrogen-bond donor catalysts for the activation of nitroalkenes. Selected 2-borylbenzoic acid derivatives gave good yields of products in the addition of indoles to nitroalkenes. Control experiments suggest that both the internal Lewis acid coordination and the carboxylic acid functionalities are critical to the optimal performance of these catalysts.

Supporting Information