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含吡啶甲酰胺配体的Cp*Ir(III)配合物催化的酮类化合物的还原胺化反应

Reductive Amination of Ketonic Compounds Catalyzed by Cp*Ir(III) Complexes Bearing a Picolinamidato Ligand.

作者信息

Tanaka Kouichi, Miki Takashi, Murata Kunihiko, Yamaguchi Ayumi, Kayaki Yoshihito, Kuwata Shigeki, Ikariya Takao, Watanabe Masahito

机构信息

Central Research Laboratory, Technology & Development Division , Kanto Chemical Co., Inc. , 7-1, Inari 1-chome , Soka-city , Saitama 340-0003 , Japan.

Department of Chemical Science and Engineering, School of Materials and Chemical Technology , Tokyo Institute of Technology , 2-12-1-E4-1 O-okayama , Meguro-ku, Tokyo 152-8552 , Japan.

出版信息

J Org Chem. 2019 Sep 6;84(17):10962-10977. doi: 10.1021/acs.joc.9b01565. Epub 2019 Aug 9.

DOI:10.1021/acs.joc.9b01565
PMID:31362498
Abstract

Cp*Ir complexes bearing a 2-picolinamide moiety serve as effective catalysts for the direct reductive amination of ketonic compounds to give primary amines under transfer hydrogenation conditions using ammonium formate as both the nitrogen and hydrogen source. The clean and operationally simple transformation proceeds with a substrate to catalyst molar ratio (S/C) of up to 20,000 at relatively low temperature and exhibits excellent chemoselectivity toward primary amines.

摘要

带有2-吡啶甲酰胺部分的Cp*Ir配合物可作为有效的催化剂,在转移氢化条件下,以甲酸铵作为氮源和氢源,将酮类化合物直接还原胺化生成伯胺。这种清洁且操作简单的转化反应在相对较低温度下,底物与催化剂的摩尔比(S/C)高达20,000时仍能进行,并且对伯胺表现出优异的化学选择性。

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引用本文的文献

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Understanding Structural Isomerism in Organoiridium Picolinamidate Complexes and its Consequences on Reactivity and Biological Properties.理解吡啶甲酰胺基铱有机配合物中的结构异构现象及其对反应活性和生物学性质的影响。
Inorg Chem Front. 2024 Nov 7;11(21):7407-7415. doi: 10.1039/d4qi01955e. Epub 2024 Sep 13.
2
Single-Site Iridium Picolinamide Catalyst Immobilized onto Silica for the Hydrogenation of CO and the Dehydrogenation of Formic Acid.单原子铱吡啶甲酰胺催化剂固载到二氧化硅上用于 CO 的加氢和甲酸的脱氢。
Inorg Chem. 2022 Jul 11;61(27):10575-10586. doi: 10.1021/acs.inorgchem.2c01640. Epub 2022 Jun 29.
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Scope and Limitations of Reductive Amination Catalyzed by Half-Sandwich Iridium Complexes Under Mild Reaction Conditions.
温和反应条件下半三明治型铱配合物催化还原胺化反应的范围与局限性
Tetrahedron Lett. 2020 Aug 6;61(32). doi: 10.1016/j.tetlet.2020.152196. Epub 2020 Jul 3.