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Breaking the Aliphatic Wall: Iridium-Catalyzed Direct Reductive Amination of Ketones and Secondary Amines

Abstract : Direct reductive amination (DRA) is a ubiquitous reaction in organic chemistry. This transformation between a carbonyl group and an amine is most often achieved using super stoichiometric amount of hazardous hydride reagents, thus being incompatible with many sensitive functional groups. DRA could also be achieved by means of chemo- or bio-catalysis, thereby attracting the interest of industry as well as academic laboratories due to their virtually perfect atomeconomy. Although DRA are well-established for substrate pairs such as aldehydes with either 1 o or 2 o amines as well as ketones with 1 o amines, the current methodologies are limited in the case of ketones with 2 o amines. Herein, we present a general DRA protocol that overcomes this major limitation by means of iridium catalysis. The applicability of the methodology is demonstrated by accessing an unprecedented range of biologically relevant tertiary amines starting from both aliphatic ketones and aliphatic amines. The choice of a disphosphane ligand (Josiphos A or Xantphos) is essential for the success of the transformation.
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https://hal.archives-ouvertes.fr/hal-03659857
Contributor : Laurent Jonchère Connect in order to contact the contributor
Submitted on : Thursday, May 12, 2022 - 10:40:25 AM
Last modification on : Wednesday, May 18, 2022 - 4:36:09 PM

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Matthieu Jouffroy, Thi-Mo Nguyen, Marie Cordier, Marielle Blot, Thierry Roisnel, et al.. Breaking the Aliphatic Wall: Iridium-Catalyzed Direct Reductive Amination of Ketones and Secondary Amines. Chemistry - A European Journal, Wiley-VCH Verlag, 2022, ⟨10.1002/chem.202201078⟩. ⟨hal-03659857⟩

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