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Synthesis 2014; 46(08): 1100-1106
DOI: 10.1055/s-0033-1340839
DOI: 10.1055/s-0033-1340839
paper
New 4-Pyridyl Nonaflates as Precursors for Push–Pull Solvatochromic Dyes
Further Information
Publication History
Received: 19 December 2013
Accepted after revision: 28 January 2014
Publication Date:
21 February 2014 (online)
Abstract
2,6-Disubstituted 4-pyridyl nonaflates including methyl, phenyl, 2-thienyl and 2-furyl groups were prepared by cyclocondensation reactions of the appropriate β-ketoenamides. Palladium-catalyzed cross-couplings (Suzuki–Miyaura, Mizoroki–Heck and Sonogashira reactions) led to buildings blocks that are direct precursors for the envisioned synthesis of push–pull solvatochromic dyes.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are experimental procedures for the synthesis of compounds 6a,b,d, 8a,b,d–j, 9d–j, 10a,b,d,e, 11a,b,d, 12a,b,d, 13a,b,d–j, 14b,d–j as well as copies of NMR spectra for all new compounds.
- Supporting Information
-
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For a general view about this phenomenon, see:
For reviews on the behavior of compounds such as 1 see:
For further details about the behavior of compounds like 3, see:
For a review about the advantages of alkenyl and aryl nonaflates in transition-metal-catalyzed reactions, see:
For recent examples utilizing pyrid-4-yl nonaflates, see: