title: Synthesis of 1-indanols and 1-indanamines by intramolecular palladium(0)-catalyzed C(sp3)-H arylation: impact of conformational effects.
abstract: 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.
authors: Université Claude Bernard Lyon 1, CNRS UMR 5246, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CPE Lyon, 43 Boulevard du 11 Novembre 1918, 69622 Villeurbanne (France).
authors: Simon
authors: S
authors: Janody
authors: Rodolphe
authors: R
authors: Jazzar
authors: Arnaud
authors: A
authors: Comte
authors: Philipp M
authors: PM
authors: Holstein
authors: Jean-Pierre
authors: JP
authors: Vors
authors: Mark J
authors: MJ
authors: Ford
authors: Olivier
authors: O
authors: Baudoin
keywords: CC coupling; CH activation; conformation analysis; palladium