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Issue 2, 2015
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Development and investigation of a site selective palladium-catalyzed 1,4-difunctionalization of isoprene using pyridine–oxazoline ligands

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Abstract

Palladium-catalyzed 1,4-difunctionalizations of isoprene that produce skipped polyenes are reported. Complex isomeric product mixtures are possible as a result of the difficult-to-control migratory insertion of isoprene into a Pd–alkenyl bond, but good site selectivity has been achieved using easily accessible pyrox ligands. Mechanistic studies suggest that the control of insertion is the result of the unique electronic asymmetry and steric properties of the ligand.

Graphical abstract: Development and investigation of a site selective palladium-catalyzed 1,4-difunctionalization of isoprene using pyridine–oxazoline ligands

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Publication details

The article was received on 07 Oct 2014, accepted on 26 Nov 2014 and first published on 28 Nov 2014


Article type: Edge Article
DOI: 10.1039/C4SC03074E
Chem. Sci., 2015,6, 1355-1361
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    Development and investigation of a site selective palladium-catalyzed 1,4-difunctionalization of isoprene using pyridine–oxazoline ligands

    M. S. McCammant and M. S. Sigman, Chem. Sci., 2015, 6, 1355
    DOI: 10.1039/C4SC03074E

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