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Extending the Scope of the B(C 6 F 5 ) 3 ‐Catalyzed CN Bond Reduction: Hydrogenation of Oxime Ethers and Hydrazones
Author(s) -
Mohr Jens,
Porwal Digvijay,
Chatterjee Indranil,
Oestreich Martin
Publication year - 2015
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.201503509
Subject(s) - chemistry , ketone , aldehyde , oxime , catalysis , toluene , medicinal chemistry , reactivity (psychology) , heterolysis , solvent , organic chemistry , lewis acids and bases , polymer chemistry , medicine , alternative medicine , pathology
The B(C 6 F 5 ) 3 ‐catalyzed hydrogenation is applied to aldoxime triisopropylsilyl ethers and hydrazones bearing an easily removable phthaloyl protective group. The CN reduction of aldehyde‐derived substrates (oxime ethers and hydrazones) is enabled by using 1,4‐dioxane as the solvent known to participate as the Lewis‐basic component in FLP‐type heterolytic dihydrogen splitting. More basic ketone‐derived hydrazones act as Lewis bases themselves in the FLP‐type dihydrogen activation and are therefore successfully hydrogenated in nondonating toluene. The difference in reactivity between aldehyde‐ and ketone‐derived substrates is also reflected in the required catalyst loading and dihydrogen pressure.