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

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
› Author Affiliations
Further Information

Publication History

Received: 09 March 2012

Accepted: 22 March 2012

Publication Date:
25 May 2012 (online)

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

 
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