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

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

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 Cp t affords...

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Bibliographic Details
Published in:Chemical science (Cambridge) Vol. 6; no. 1; pp. 254 - 258
Main Authors: Hyster, Todd K., Dalton, Derek M., Rovis, Tomislav
Format: Journal Article
Language:English
Published: 01-01-2015
Subjects:
Activation
Aliphatic compounds
Alkenes
Bearing
Crystallography
Ligands
Selectivity
Synthesis
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Summary: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 Cp t 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.
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ISSN:2041-6520
2041-6539
DOI:10.1039/C4SC02590C