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Issue 1, 2015
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Ligand design for Rh(III)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones

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Abstract

We report the regioselective synthesis of dihydroisoquinolones from aliphatic alkenes and O-pivaloyl benzhydroxamic acids mediated by a Rh(III) precatalyst bearing sterically bulky substituents. While the prototypical Cp* ligand provides product with low selectivity, sterically bulky Cpt affords product with excellent regioselectivity for a range of benzhydroxamic acids and alkenes. Crystallographic evidence offers insight as to the source of the increased regioselectivity.

Graphical abstract: Ligand design for Rh(iii)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones

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Publication details

The article was received on 25 Aug 2014, accepted on 22 Sep 2014 and first published on 01 Oct 2014


Article type: Edge Article
DOI: 10.1039/C4SC02590C
Citation: Chem. Sci., 2015,6, 254-258
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    Ligand design for Rh(III)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones

    T. K. Hyster, D. M. Dalton and T. Rovis, Chem. Sci., 2015, 6, 254
    DOI: 10.1039/C4SC02590C

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