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

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

16 Citations (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.

Original language	English
Journal	Chemistry - A European Journal
Volume	24
Issue	56
Pages (from-to)	14946-14949
Number of pages	4
ISSN	0947-6539
DOIs	https://doi.org/10.1002/chem.201804077
Publication status	Published - 9 Oct 2018

Keywords

alkylzinc reagents
aminocarbonylation
isotope labeling
nickel
pincer complexes

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10.1002/chem.201804077

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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",

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year = "2018",

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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.
In: Chemistry - A European Journal, Vol. 24, No. 56, 09.10.2018, p. 14946-14949.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

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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

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DO - 10.1002/chem.201804077

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SN - 0947-6539

VL - 24

SP - 14946

EP - 14949

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 56

ER -

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

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Keywords

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