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使用一氧化碳和羧酸衍生物的催化还原N-烷基化反应:近期进展与发展

Catalytic Reductive N-Alkylations Using CO and Carboxylic Acid Derivatives: Recent Progress and Developments.

作者信息

Cabrero-Antonino Jose R, Adam Rosa, Beller Matthias

机构信息

Leibniz-Institut für Katalyse, Homogeneous Catalysis, Albert-Einstein-Strasse 29a, Rostock, 18059, Germany.

Instituto de Tecnología Química. Universitat Politécnica de València-Consejo Superior Investigaciones Científicas (UPV-CSIC), Avda. de los Naranjos s/n, València, 46022, Spain.

出版信息

Angew Chem Int Ed Engl. 2019 Sep 9;58(37):12820-12838. doi: 10.1002/anie.201810121. Epub 2019 Jun 5.

DOI:10.1002/anie.201810121
PMID:30306704
Abstract

N-Alkylamines are key intermediates in the synthesis of fine chemicals, dyes, and natural products, and hence are highly valuable building blocks in organic chemistry. Consequently, the development of greener and more efficient procedures for their production continues to attract the interest of both academic and industrial chemists. Reductive procedures such as reductive amination or N-alkylation through hydrogen autotransfer by employing carbonyl compounds or alcohols as alkylating agents have prevailed for the synthesis of amines. In the last few years, carboxylic/carbonic acid derivatives and CO have been introduced as alternative and convenient alkylating sources. The safety, easy accessibility, and high stability of these reagents makes the development of new reductive transformations with them as N-alkylating agents a useful alternative to existing procedures. In this Review, we summarize reported examples of one-pot reductive N-alkylation methods that use carboxylic/carbonic acid derivatives or CO as alkylating agents.

摘要

N-烷基胺是精细化学品、染料和天然产物合成中的关键中间体,因此是有机化学中极具价值的结构单元。因此,开发更绿色、更高效的生产方法一直吸引着学术界和工业界化学家的关注。通过使用羰基化合物或醇作为烷基化剂进行还原胺化或通过氢自转移进行N-烷基化等还原方法在胺的合成中占主导地位。在过去几年中,羧酸/碳酸衍生物和CO已被引入作为替代且方便的烷基化源。这些试剂的安全性、易于获取性和高稳定性使得开发以它们作为N-烷基化剂的新还原转化方法成为现有方法的一种有用替代方案。在本综述中,我们总结了报道的使用羧酸/碳酸衍生物或CO作为烷基化剂的一锅法还原N-烷基化方法的实例。

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