Solid Molecular Frustrated Lewis Pairs in a Polyamine Organic Framework for the Catalytic Metal‐free Hydrogenation of Alkenes

Willms, Andrea; Schumacher, Hannah; Tabassum, Tarnuma; Qi, Long; Scott, Susannah L.; Hausoul, Peter J. C.; Rose, Marcus

doi:10.1002/cctc.201701783

Solid Molecular Frustrated Lewis Pairs in a Polyamine Organic Framework for the Catalytic Metal‐free Hydrogenation of Alkenes

Journal Article · Thu Feb 08 23:00:00 EST 2018 · ChemCatChem

DOI:https://doi.org/10.1002/cctc.201701783· OSTI ID:1420002

^[1]; Schumacher, Hannah ^[1]; Tabassum, Tarnuma ^[2]; Qi, Long ^[3]; Scott, Susannah L. ^[3]; ^[1]; ^[4]

Institut für Technische und Makromolekulare Chemie RWTH Aachen University Worringerweg 2 52074 Aachen Germany
Department of Chemistry &, Biochemistry University of California Santa Barbara CA 93106 USA
Department of Chemistry &, Biochemistry University of California Santa Barbara CA 93106 USA, Department of Chemical Engineering University of California Santa Barbara CA 93106 USA
Institut für Technische und Makromolekulare Chemie RWTH Aachen University Worringerweg 2 52074 Aachen Germany, Ernst-Berl-Institut Technische Chemie II Technische Universität Darmstadt Alarich-Weiss-Straße 8 64287 Darmstadt Germany

Abstract

We report for the first time a metal‐free heterogeneously catalyzed hydrogenation using a semi‐solid frustrated Lewis pair (FLP). The catalyst consists of a solid polyamine organic framework and molecular tris(pentafluorophenyl)borane (BCF) that form a semi‐immobilized FLP in situ in the catalytic hydrogenation of diethyl benzylidenemalonate. ¹¹ B NMR spectroscopy proves the successful hydrogen activation by the FLP. Furthermore, the B−N interactions between the polyamine and BCF are investigated by IR and solid state NMR spectroscopy. The FLP 1,4‐diazabicyclo[2.2.2]octane (DABCO)/BCF, which combines the features of a FLP and a classical Lewis adduct, functions as molecular reference in both, catalysis and characterization. Furthermore, computational studies enable a better insight into the hydrogen activation through DABCO/BCF and polyamine/BCF.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

Grant/Contract Number:: NONE; FG02-03ER15467

OSTI ID:: 1420002

Alternate ID(s):: OSTI ID: 1537512

Journal Information:: ChemCatChem, Journal Name: ChemCatChem Journal Issue: 8 Vol. 10; ISSN 1867-3880

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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