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Synthesis 2014; 46(16): 2143-2148
DOI: 10.1055/s-0033-1338659
DOI: 10.1055/s-0033-1338659
practical synthetic procedures
Conversion of Aromatic Amino into Trifluoromethyl Groups through a Sandmeyer-Type Transformation
Further Information
Publication History
Received: 18 March 2014
Accepted after revision: 12 June 2014
Publication Date:
24 July 2014 (online)
Abstract
A novel strategy for aromatic trifluoromethylation by converting amino into trifluoromethyl groups via a Sandmeyer-type reaction is reported. The transformation involves diazotization of the aromatic amines with tert-butyl nitrite and hydrochloric acid to form aryldiazonium chlorides, followed by trifluoromethylation with trifluoromethylsilver at low temperature. Various readily available aromatic amines are smoothly converted under mild conditions.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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For reviews, see:
For recent reports, see:
For trifluoromethylation via transition-metal-catalyzed C–H bond activation, see:
For recent reviews on arenediazonium salts, see: