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Solid Molecular Frustrated Lewis Pairs in a Polyamine Organic Framework for the Catalytic Metal‐free Hydrogenation of Alkenes
Author(s) -
Willms Andrea,
Schumacher Hannah,
Tabassum Tarnuma,
Qi Long,
Scott Susannah L.,
Hausoul Peter J. C.,
Rose Marcus
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201701783
Subject(s) - dabco , frustrated lewis pair , chemistry , borane , catalysis , ammonia borane , octane , adduct , lewis acids and bases , polyamine , nuclear magnetic resonance spectroscopy , combinatorial chemistry , organic chemistry , hydrogen production , biochemistry
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.