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A Molecularly Defined Iron‐Catalyst for the Selective Hydrogenation of α,β‐Unsaturated Aldehydes
Author(s) -
Wienhöfer Gerrit,
Westerhaus Felix A.,
Junge Kathrin,
Ludwig Ralf,
Beller Matthias
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300660
Subject(s) - chemoselectivity , trifluoroacetic acid , catalysis , chemistry , hydride , allylic rearrangement , organic chemistry , aldehyde , catalytic cycle , in situ , medicinal chemistry , combinatorial chemistry , hydrogen
A selective iron‐based catalyst system for the hydrogenation of α,β‐unsaturated aldehydes to allylic alcohols is presented. Applying the defined iron–tetraphos complex [FeF(L)][BF 4 ] (L=P(PhPPh 2 ) 3 ) in the presence of trifluoroacetic acid a broad range of aldehydes are reduced in high yields using low catalyst loadings (0.05–1 mol %). Excellent chemoselectivity for the reduction of aldehydes in the presence of other reducible moieties, for example, ketones, olefins, esters, etc. is achieved. Based on the in situ detected hydride species [FeH(H 2 )(L)] + a catalytic cycle is proposed that is supported by computational calculations.