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

• Published in: Angewandte Chemie International Edition
• Main Authors: Cabrero Antonino, Jose Ramón, Adam-Ortiz, Rosa, Beller, Matthias
• Other Authors: Universitat Politècnica de València. Departamento de Química - Departament de Química, Bundesministerium für Bildung und Forschung, Alemania
• Format: Article in Journal/Newspaper
• Language: English
• Published: John Wiley & Sons 2019
• Subjects: Carbon dioxide; Carboxylic; Carbonic acid derivatives; Heterocycles; N-alkylation; Reductive transformations; QUIMICA ORGANICA; Cierva; Ortiz; Carbonic acid
• Online Access: http://hdl.handle.net/10251/153458; https://doi.org/10.1002/anie.201810121

This is the peer reviewed version of the following article: Angew. Chem. Int. Ed. 2019, 58, 12820 12838, which has been published in final form at https://doi.org/10.1002/anie.201810121. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. [EN] 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. This work was supported by the state of MecklenburgVorpommern and the BMBF. J.R.C.-A. thanks the Ministerio de Ciencia, Innovacion y Universidades for a Juan de la Cierva contract. R.A. thanks UPV for a postdoctoral contract. Cabrero Antonino, JR.; Adam-Ortiz, R.; Beller, M. (2019). Catalytic Reductive N-Alkylations Using CO2 and Carboxylic Acid Derivatives: Recent Progress and Developments. Angewandte Chemie International Edition. 58(37):12820-12838. https://doi.org/10.1002/anie.201810121 S 12820 12838 58 37 Adams, J. M., & Cory, S. (1975). Modified nucleosides and bizarre 5′-termini in mouse myeloma mRNA. Nature, 255(5503), 28-33. doi:10.1038/255028a0 ...