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Efficient Synthesis of Amines by Iron‐Catalyzed C=N Transfer Hydrogenation and C=O Reductive Amination
Author(s) -
Facchini Sofia Vailati,
Cettolin Mattia,
Bai Xishan,
Casamassima Giuseppe,
Pignataro Luca,
Gennari Cesare,
Piarulli Umberto
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701316
Subject(s) - chemistry , reductive amination , catalysis , transfer hydrogenation , imine , aryl , yield (engineering) , amination , organic chemistry , alkyl , combinatorial chemistry , medicinal chemistry , materials science , ruthenium , metallurgy
Here we report the catalytic transfer hydrogenation (CTH) of non‐activated imines promoted by a Fe‐catalyst in the absence of Lewis acid co‐catalysts. Use of the (cyclopentadienone)iron complex 1 , which is much more active than the classical ‘Knölker complex’ 2 , allowed to reduce a number of N‐aryl and N‐alkyl imines in very good yields using i PrOH as hydrogen source. The reaction proceeds with relatively low catalyst loading (0.5–2 mol%) and, remarkably, its scope includes also ketimines, whose reduction with a Fe‐complex as the only catalyst has little precedents. Based on this methodology, we developed a one‐pot CTH protocol for the reductive amination of aldehydes/ketones, which provides access to secondary amines in high yield without the need to isolate imine intermediates.