Catalytic Reductive N‐Alkylations Using CO2 and Carboxylic Acid Derivatives: Recent Progress and Developments

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 bot...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-09, Vol.58 (37), p.12820-12838
Main Authors: Cabrero‐Antonino, Jose R., Adam, Rosa, Beller, Matthias
Format: Article
Language:English
Subjects:
Alcohols
Alkylamines
Alkylating agents
Alkylation
Amination
Amines
Carbon dioxide
Carbonic acid
Carbonyl compounds
Carbonyls
Carboxylic acids
carboxylic/carbonic acid derivatives
Catalysis
Chemists
Derivatives
Fine chemicals
heterocycles
Intermediates
N-alkylation
Natural products
Organic chemistry
Reagents
reductive transformations
Synthesis
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Summary: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 CO2 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 CO2 as alkylating agents. Oxidized alkyl partners in reductive N‐alkylations: CO2 and carboxylic/carbonic acid derivatives can be employed as safe and readily available N‐alkylating agents in reductive methods to give a wide range of N‐alkylamines and heterocycles. This Review gives an overview of these processes.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201810121