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Synlett 2014; 25(20): 2891-2894
DOI: 10.1055/s-0034-1379481
DOI: 10.1055/s-0034-1379481
letter
Chemoselective Zinc/HCl Reduction of Halogenated β-Nitrostyrenes: Synthesis of Halogenated Dopamine Analogues
Further Information
Publication History
Received: 13 June 2014
Accepted after revision: 22 September 2014
Publication Date:
29 October 2014 (online)
Abstract
A detailed account regarding the synthesis of 2- and 5-halogenated dopamine is given. The key step is a chemoselective reduction of a nitrostyrene by Zn/HCl at 0 °C. These conditions represent a simple, low-cost alternative to reduction by water-sensitive hydride donors and two-step procedures. Under these conditions, aryl fluoride, chloride, and bromide groups are stable. However, iodine undergoes significant reductive dehalogenation.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- Supporting Information
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