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Synthesis 2012; 44(14): 2173-2180
DOI: 10.1055/s-0031-1291048
DOI: 10.1055/s-0031-1291048
special topic
Internal Lewis Acid Assisted Benzoic Acid Catalysis
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
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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For examples of internal Lewis acid assisted ureas in the context of molecular recognition, see:
For selected recent examples of carboxylic acids operating as hydrogen-bond-donor catalysts, see:
For examples of internal activation of carbonyl functionalities with boron in structures similar to 8a, see: