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Early Main Group Metal Catalysts for Imine Hydrosilylation
Author(s) -
Elsen Holger,
Fischer Christian,
Knüpfer Christian,
Escalona Ana,
Harder Sjoerd
Publication year - 2019
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.201904148
Subject(s) - phenylsilane , chemistry , catalysis , imine , stoichiometry , aldimine , metal , aryl , medicinal chemistry , alkyl , hydride , organic chemistry
The efficient catalytic reduction of imines with phenylsilane is achieved by using the potassium, calcium and strontium based catalysts [(DMAT)K (THF)] ∞ , (DMAT) 2 Ca⋅(THF) 2 and (DMAT) 2 Sr⋅(THF) 2 (DMAT=2‐dimethylamino‐α‐trimethylsilylbenzyl). Eight different aldimines and the ketimine Ph 2 C=NPh could be successfully reduced by PhSiH 3 at temperatures between 25–60 °C with catalyst loadings down to 2.5 mol %. Also, simple amides like KN(SiMe 3 ) 2 or Ae[N(SiMe 3 ) 2 ] 2 (Ae=Ca, Sr, Ba) catalyze this reaction. Activities increase with metal size. For most substrates the activity increases along the row K