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Ligand Design for Rh(III)-Catalyzed C-H Activation: An Unsymmetrical Cyclopentadienyl Enables a Regioselective Synthesis of Dihydroisoquinolones.


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.

SUBMITTER: Hyster TK 

PROVIDER: S-EPMC4256080 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

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Ligand Design for Rh(III)-Catalyzed C-H Activation: An Unsymmetrical Cyclopentadienyl Enables a Regioselective Synthesis of Dihydroisoquinolones.

Hyster Todd K TK   Dalton Derek M DM   Rovis Tomislav T  

Chemical science 20150101 1


We report the regioselective synthesis of dihydroisoquinolones from aliphatic alkenes and <i>O</i>-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 Cp<sup>t</sup> 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. ...[more]

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