2,3-Diamino-4,5-diarylcyclopentadienone iron carbonyl complexes as catalysts for reductive amination reactions†

IF 5.4 3区材料科学 Q2 CHEMISTRY, PHYSICAL

ACS Applied Energy Materials Pub Date : 2024-08-12 DOI:10.1039/d4cy00372a

Lukas Körner , Dirk Bockfeld , Thomas Bannenberg , Matthias Tamm

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Abstract

The reaction of dipiperidinoacetylene, (CH₂)₅NCCN(CH₂)₅, with a series of 2,3-diarylcyclopropenones (Ar)₂C₃O (Ar = phenyl, 4-tert-butylphenyl, 2,5-dimethylphenyl, 4-trifluoromethylphenyl) afforded 2,3-dipiperidino-4,5-diarylcyclopentadienones, which were used to prepare cyclopentadienone (CPD) iron tricarbonyl complexes [(CPD)Fe(CO)₃] by the reaction with Fe₂(CO)₉. Subsequent treatment with trimethylamine-N-oxide in the presence of acetonitrile afforded the corresponding acetonitrile complexes [(CPD)Fe(CO)₂(NCCH₃)], which were used as catalysts for the reductive amination of citronellal with various secondary amines under 5 bar of dihydrogen pressure. The first iron-catalysed reductive amination for the preparation of the pharmaceutically important antidepressant sertraline is also reported.

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作为还原胺化反应催化剂的 2,3-二氨基-4,5-二芳基环戊二烯酮铁羰基复合物

二哌啶基乙炔（(CH2)5NCCN(CH2)5）与一系列 2,3-二芳基环丙烯酮（Ar）2C3O（Ar = 苯基、4-叔丁基苯基、2,5-二甲基苯基、4-三氟甲基苯基）反应得到 2、与 Fe2(CO)9 反应制备环戊二烯酮（CPD）三羰基铁络合物 [(CPD)Fe(CO)3]。随后在乙腈存在下用三甲胺-N-氧化物进行处理，得到了相应的乙腈络合物[(CPD)Fe(CO)2(NCCH3)]，并将其用作催化剂，在 5 巴二氢压力下将香茅醛与各种仲胺进行还原胺化反应。报告还首次报道了铁催化还原胺化反应制备具有重要药用价值的抗抑郁药舍曲林。

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来源期刊

ACS Applied Energy Materials Materials Science-Materials Chemistry

CiteScore

10.30

自引率

6.20%

发文量

1368

期刊介绍： ACS Applied Energy Materials is an interdisciplinary journal publishing original research covering all aspects of materials, engineering, chemistry, physics and biology relevant to energy conversion and storage. The journal is devoted to reports of new and original experimental and theoretical research of an applied nature that integrate knowledge in the areas of materials, engineering, physics, bioscience, and chemistry into important energy applications.