A chiral porous organic polymer as a heterogeneous ligand for enantioselective Pd-catalyzed C(sp3)-H functionalization

Niklas Rosendal Bennedsen, Søren Kramer, Søren Kegnæs*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Catalytic enantioselective C(sp3)-H functionalization remains a difficult task, even more so using heterogeneous catalysts. Here, we report the first example of enantioselective C(sp3)-H functionalization using a chiral porous organic polymer as the heterogeneous catalyst. The catalyst consists of a polystyrene-incorporating chiral phosphoramidite coordinated to palladium, and it provides up to 86% ee for the challenging enantioselective C(sp3)-H functionalization of a range of 3-Arylpropanamides. The swelling properties of the catalyst allow for quasi-homogeneous behavior in the reaction mixture while still enabling easy catalyst separation from the reaction medium and reuse. Thorough characterization of the fresh porous organic polymer and recycled catalyst material by 31P CP/MAS NMR, 13C-1H CP/MAS NMR, X-ray diffraction, TEM, STEM, EDX-SEM, ICP, and XRF in combination with modifications to the reaction conditions for the recycled catalyst material reveals potential explanations for catalyst deactivation.
Original languageEnglish
JournalCatalysis Science and Technology
Volume10
Issue number22
Pages (from-to)7697-7705
ISSN2044-4753
DOIs
Publication statusPublished - 2020

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