Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride. / Airoldi, Veronica; Piccolo, Oreste; Roda, Gabriella; Appiani, Rebecca; Bavo, Francesco; Tassini, Riccardo; Paganelli, Stefano; Arnoldi, Sebastiano; Pallavicini, Marco; Bolchi, Cristiano.

In: European Journal of Organic Chemistry, Vol. 2020, No. 2, 16.01.2020, p. 162-168.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Airoldi, V, Piccolo, O, Roda, G, Appiani, R, Bavo, F, Tassini, R, Paganelli, S, Arnoldi, S, Pallavicini, M & Bolchi, C 2020, 'Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride', European Journal of Organic Chemistry, vol. 2020, no. 2, pp. 162-168. https://doi.org/10.1002/ejoc.201901614

APA

Airoldi, V., Piccolo, O., Roda, G., Appiani, R., Bavo, F., Tassini, R., Paganelli, S., Arnoldi, S., Pallavicini, M., & Bolchi, C. (2020). Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride. European Journal of Organic Chemistry, 2020(2), 162-168. https://doi.org/10.1002/ejoc.201901614

Vancouver

Airoldi V, Piccolo O, Roda G, Appiani R, Bavo F, Tassini R et al. Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride. European Journal of Organic Chemistry. 2020 Jan 16;2020(2):162-168. https://doi.org/10.1002/ejoc.201901614

Author

Airoldi, Veronica ; Piccolo, Oreste ; Roda, Gabriella ; Appiani, Rebecca ; Bavo, Francesco ; Tassini, Riccardo ; Paganelli, Stefano ; Arnoldi, Sebastiano ; Pallavicini, Marco ; Bolchi, Cristiano. / Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride. In: European Journal of Organic Chemistry. 2020 ; Vol. 2020, No. 2. pp. 162-168.

Bibtex

@article{5efec97e23194f3bb030d42257817de5,
title = "Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride",
abstract = "A one-pot reductive amination of aldehydes and ketones with NaBH4 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 NaBH4. 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.",
keywords = "Amination, Aquivion, Chemoselectivity, Cinacalcet, Sodium borohydride",
author = "Veronica Airoldi and Oreste Piccolo and Gabriella Roda and Rebecca Appiani and Francesco Bavo and Riccardo Tassini and Stefano Paganelli and Sebastiano Arnoldi and Marco Pallavicini and Cristiano Bolchi",
year = "2020",
month = jan,
day = "16",
doi = "10.1002/ejoc.201901614",
language = "English",
volume = "2020",
pages = "162--168",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "2",

}

RIS

TY - JOUR

T1 - Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride

AU - Airoldi, Veronica

AU - Piccolo, Oreste

AU - Roda, Gabriella

AU - Appiani, Rebecca

AU - Bavo, Francesco

AU - Tassini, Riccardo

AU - Paganelli, Stefano

AU - Arnoldi, Sebastiano

AU - Pallavicini, Marco

AU - Bolchi, Cristiano

PY - 2020/1/16

Y1 - 2020/1/16

N2 - A one-pot reductive amination of aldehydes and ketones with NaBH4 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 NaBH4. 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.

AB - A one-pot reductive amination of aldehydes and ketones with NaBH4 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 NaBH4. 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.

KW - Amination

KW - Aquivion

KW - Chemoselectivity

KW - Cinacalcet

KW - Sodium borohydride

UR - http://www.scopus.com/inward/record.url?scp=85076007006&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201901614

DO - 10.1002/ejoc.201901614

M3 - Journal article

AN - SCOPUS:85076007006

VL - 2020

SP - 162

EP - 168

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 2

ER -

ID: 259878939