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Published Erratum
. 2010 Jul 24;66(30):5720-5726.
doi: 10.1016/j.tet.2010.05.063.

Corrigendum to Solvent-dependent oxidative coupling of 1-aryl-1,3-dicarbonyls and styrene

Brian M Casey  1 , Cynthia A Eakin, Jingliang Jiao, Dhandapani V Sadasivam, Robert A Flowers
Affiliations
Published Erratum

Corrigendum to Solvent-dependent oxidative coupling of 1-aryl-1,3-dicarbonyls and styrene

Brian M Casey et al. Tetrahedron. .

Abstract

This report describes the scope and mechanism of the solvent-dependent, chemoselective oxidative coupling of 1-aryl-1,3-dicarbonyls with styrene using Ce(IV) reagents. Dihydrofuran derivatives are obtained when reactions are performed in methanol whereas nitrate esters can be selectively synthesized in acetonitrile and methylene chloride. Mechanistic studies are consistent with the rate of solvent-assisted deprotonation of a radical cation intermediate playing an integral role in the selective formation of products.

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Figures

Figure 1
Figure 1
Time-resolved absorption spectrum observed from CTAN and ethylbenzoylacetate (3) in CH2Cl2 ([3] = 50 mM, [CTAN] = 1 mM) from 400–500 nm at 25°C. Spectrum was obtained by taking 10 scans every 5 nm over a period of 50 msec.
Scheme 1
Scheme 1
Solvent-dependent synthesis of 2-allylated 1,3-dicarbonyl and dihydrofuran derivatives.
Scheme 2
Scheme 2
Proposed mechanism for the solvent-dependent chemoselective oxidative addition of 1-aryl-1,3-dicarbonyls to styrene.
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