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Efficient One‐Pot Reductive Aminations of Carbonyl Compounds with Aquivion‐Fe as a Recyclable Catalyst and Sodium Borohydride
Author(s) -
Airoldi Veronica,
Piccolo Oreste,
Roda Gabriella,
Appiani Rebecca,
Bavo Francesco,
Tassini Riccardo,
Paganelli Stefano,
Arnoldi Sebastiano,
Pallavicini Marco,
Bolchi Cristiano
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901614
Subject(s) - chemistry , reductive amination , sodium borohydride , chemoselectivity , catalysis , organic chemistry , amination , methanol , combinatorial chemistry
A one‐pot reductive amination of aldehydes and ketones with NaBH 4 was developed with a view to providing efficient, economical and greener synthetic conditions. A recyclable iron‐based Lewis catalyst, Aquivion‐Fe, was used to promote imine formation in cyclopentyl methyl ether, followed by the addition of a small amount of methanol to the reaction mixture to enable C=N reduction by NaBH 4 . The protocol, applied to a wide number of amines and carbonyl compounds, resulted in ever complete conversion of these latter with excellent chemoselectivity towards the expected amination products in the most cases. Isolated yields, determined for a selection of the screened substrates, were found consistent with the previously obtained conversion and selectivity data. Cinacalcet, an important active pharmaceutical ingredient, was efficiently prepared by the title procedure.