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Issue 5, 2015
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Palladium-catalyzed cross-coupling of α-bromocarbonyls and allylic alcohols for the synthesis of α-aryl dicarbonyl compounds

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Abstract

The palladium-catalyzed coupling of olefins and organohalides is a versatile approach for synthesizing complex molecules from simple starting materials. We have developed a palladium-catalyzed coupling of α-bromocarbonyl compounds with allylic alcohols for the generation of acyclic aryl-substituted dicarbonyl compounds. The reaction proceeds via a tandem olefin insertion of an α-acyl radical followed by a 1,2-aryl migration. In addition to providing preliminary evidence for a free radical mediated mechanism, we demonstrate unprecedented levels of 1,3-stereoinduction for the 1,2-migration step.

Graphical abstract: Palladium-catalyzed cross-coupling of α-bromocarbonyls and allylic alcohols for the synthesis of α-aryl dicarbonyl compounds

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Publication details

The article was received on 10 Feb 2015, accepted on 25 Feb 2015 and first published on 17 Mar 2015


Article type: Edge Article
DOI: 10.1039/C5SC00505A
Citation: Chem. Sci., 2015,6, 2777-2781
  • Open access: Creative Commons BY-NC license
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    Palladium-catalyzed cross-coupling of α-bromocarbonyls and allylic alcohols for the synthesis of α-aryl dicarbonyl compounds

    Y. Yu and U. K. Tambar, Chem. Sci., 2015, 6, 2777
    DOI: 10.1039/C5SC00505A

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