Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 35, Pages 11084-11090Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201402907
Keywords
C-C coupling; C-H activation; conformation analysis; palladium
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Funding
- Bayer CropScience AG
- Ministere de l'Enseignement Superieur et de la Recherche
- Institut Universitaire de France
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A range of valuable 1-indanols and 1-indanamines containing a tertiary C1 atom were synthesized by intramolecular palladium(0)-catalyzed C(sp(3))-H arylation, despite unfavorable steric interactions. The efficiency of the reaction was found to correlate with the degree of substitution at C2, as expected from the Thorpe-Ingold effect. Additionally, the nature of the heteroatomic substituent at C1 had a marked influence on the diastereoselectivity at C1 and C2; indeed, 1-indanols and 1-indanamines were obtained with the opposite relative configuration. Analysis of the X-ray and DFT-optimized structures of the corresponding reactive intermediates provided useful insights into the subtle conformational effects induced by these substituents.
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