Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2012; 23(18): 2699-2703
DOI: 10.1055/s-0032-1317485
DOI: 10.1055/s-0032-1317485
letter
Brønsted Acid Catalyzed Friedel–Crafts Alkylation Reactions of Trifluoromethyl-α,β-ynones with Indoles
Further Information
Publication History
Received: 18 August 2012
Accepted after revision: 25 September 2012
Publication Date:
18 October 2012 (online)


Abstract
The successful development of a Brønsted acid catalyzed Friedel–Crafts alkylation reaction between trifluoromethyl-α,β-ynones and indoles has been described. The reaction is catalyzed by benzoic acid (5 mol%), with the indoles adding to the carbonyl carbon of the trifluoromethyl-α,β-ynones producing the corresponding 1,2-addition products as trifluoromethyl propargyl alcohols in high yields. Furthermore, treatment of the product with indoles in the presence of trifluoroacetic acid (10 mol%) afforded trifluoromethyl-functionalized unsymmetrical bis(indolyl)propynes in high yields.
Key words
Brønsted acid - trifluoromethyl-α,β-ynones - indoles - trifluoromethyl propargyl alcohols - bis(indolyl)propynesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information