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Synthesis 2012; 44(20): 3165-3170
DOI: 10.1055/s-0032-1317134
DOI: 10.1055/s-0032-1317134
paper
Highly Improved Copper-Mediated Michael Addition of Ethyl Bromodifluoroacetate in the Presence of Protic Additive
Further Information
Publication History
Received: 07 June 2012
Accepted after revision: 26 July 2012
Publication Date:
03 September 2012 (online)
Abstract
Copper-mediated Michael addition of ethyl bromodifluoroacetate to Michael acceptors is accompanied by the formation of a substantial amount of byproducts. Elucidation of their structure hinted the cause of their formation, from which we discovered a highly improved and robust protocol by treatment with protic additives such as H2O and AcOH. This modification led to significant increase of yield with concomitant decreased use of reagent.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are spectroscopic data (1H and 13C NMR spectra of the Michael adducts, 4a–h, and byproduct 6a).
- Supporting Information
-
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