Synthesis of Aliphatic Carboxamides Mediated by Nickel NN2-Pincer Complexes and Adaption to Carbon Isotope-Labeling

Karoline Thorum Neumann; Aske Skyum Donslund; Thomas Andersen; Dennis Ulsøe Nielsen; Troels Skrydstrup

doi:10.1002/chem.201804077

Synthesis of Aliphatic Carboxamides Mediated by Nickel NN₂-Pincer Complexes and Adaption to Carbon Isotope-Labeling

Karoline Thorum Neumann, Aske Skyum Donslund, Thomas Andersen, Dennis Ulsøe Nielsen, Troels Skrydstrup

Publikation: Bidrag til tidsskrift/Konferencebidrag i tidsskrift /Bidrag til avis › Tidsskriftartikel › Forskning › peer review

16 Citationer (Scopus)

Abstract

The development of a nickel-mediated aminocarbonylation utilizing NN ₂-pincer Ni-complexes, alkylzinc reagents, stoichiometric carbon monoxide and amines is described for the first time, which can be adapted to late-stage carbon-isotope labeling. This work expands the scope of the highly established palladium-promoted version of the reaction, by allowing carbon-sp ³ fragments to take part in the three-component reaction. Finally, the results obtained show a remarkable effect of the pincer ligand for the reductive elimination step with the amine, which is followed by ¹³C NMR spectroscopy studies.

Originalsprog	Engelsk
Tidsskrift	Chemistry - A European Journal
Vol/bind	24
Nummer	56
Sider (fra-til)	14946-14949
Antal sider	4
ISSN	0947-6539
DOI	https://doi.org/10.1002/chem.201804077
Status	Udgivet - 9 okt. 2018

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Citationsformater

@article{3379840ad0e54bf89e0120623f20c721,

title = "Synthesis of Aliphatic Carboxamides Mediated by Nickel NN2-Pincer Complexes and Adaption to Carbon Isotope-Labeling",

abstract = "The development of a nickel-mediated aminocarbonylation utilizing NN 2-pincer Ni-complexes, alkylzinc reagents, stoichiometric carbon monoxide and amines is described for the first time, which can be adapted to late-stage carbon-isotope labeling. This work expands the scope of the highly established palladium-promoted version of the reaction, by allowing carbon-sp 3 fragments to take part in the three-component reaction. Finally, the results obtained show a remarkable effect of the pincer ligand for the reductive elimination step with the amine, which is followed by 13C NMR spectroscopy studies.",

keywords = "alkylzinc reagents, aminocarbonylation, isotope labeling, nickel, pincer complexes",

author = "Neumann, {Karoline Thorum} and Donslund, {Aske Skyum} and Thomas Andersen and Nielsen, {Dennis Uls{\o}e} and Troels Skrydstrup",

year = "2018",

month = oct,

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doi = "10.1002/chem.201804077",

language = "English",

volume = "24",

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journal = "Chemistry - A European Journal",

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publisher = "Wiley-VCH Verlag",

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}

Synthesis of Aliphatic Carboxamides Mediated by Nickel NN₂-Pincer Complexes and Adaption to Carbon Isotope-Labeling. / Neumann, Karoline Thorum; Donslund, Aske Skyum; Andersen, Thomas et al.
I: Chemistry - A European Journal, Bind 24, Nr. 56, 09.10.2018, s. 14946-14949.

Publikation: Bidrag til tidsskrift/Konferencebidrag i tidsskrift /Bidrag til avis › Tidsskriftartikel › Forskning › peer review

TY - JOUR

T1 - Synthesis of Aliphatic Carboxamides Mediated by Nickel NN2-Pincer Complexes and Adaption to Carbon Isotope-Labeling

AU - Neumann, Karoline Thorum

AU - Donslund, Aske Skyum

AU - Andersen, Thomas

AU - Nielsen, Dennis Ulsøe

AU - Skrydstrup, Troels

PY - 2018/10/9

Y1 - 2018/10/9

N2 - The development of a nickel-mediated aminocarbonylation utilizing NN 2-pincer Ni-complexes, alkylzinc reagents, stoichiometric carbon monoxide and amines is described for the first time, which can be adapted to late-stage carbon-isotope labeling. This work expands the scope of the highly established palladium-promoted version of the reaction, by allowing carbon-sp 3 fragments to take part in the three-component reaction. Finally, the results obtained show a remarkable effect of the pincer ligand for the reductive elimination step with the amine, which is followed by 13C NMR spectroscopy studies.

AB - The development of a nickel-mediated aminocarbonylation utilizing NN 2-pincer Ni-complexes, alkylzinc reagents, stoichiometric carbon monoxide and amines is described for the first time, which can be adapted to late-stage carbon-isotope labeling. This work expands the scope of the highly established palladium-promoted version of the reaction, by allowing carbon-sp 3 fragments to take part in the three-component reaction. Finally, the results obtained show a remarkable effect of the pincer ligand for the reductive elimination step with the amine, which is followed by 13C NMR spectroscopy studies.

KW - alkylzinc reagents

KW - aminocarbonylation

KW - isotope labeling

KW - nickel

KW - pincer complexes

UR - http://www.scopus.com/inward/record.url?scp=85053497202&partnerID=8YFLogxK

U2 - 10.1002/chem.201804077

DO - 10.1002/chem.201804077

M3 - Journal article

C2 - 30106491

SN - 0947-6539

VL - 24

SP - 14946

EP - 14949

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 56