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Access to β-Ketonitriles through Nickel-Catalyzed Carbonylative Coupling of α-Bromonitriles with Alkylzinc Reagents

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Access to β-Ketonitriles through Nickel-Catalyzed Carbonylative Coupling of α-Bromonitriles with Alkylzinc Reagents. / Donslund, Aske S.; Neumann, Karoline T.; Corneliussen, Nicklas P.; Grove, Ebbe K.; Herbstritt, Domenique; Daasbjerg, Kim; Skrydstrup, Troels.

In: Chemistry - A European Journal, Vol. 25, No. 42, 07.2019, p. 9856-9860.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaperJournal articleResearchpeer-review

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Donslund AS, Neumann KT, Corneliussen NP, Grove EK, Herbstritt D, Daasbjerg K et al. Access to β-Ketonitriles through Nickel-Catalyzed Carbonylative Coupling of α-Bromonitriles with Alkylzinc Reagents. Chemistry - A European Journal. 2019 Jul;25(42):9856-9860. https://doi.org/10.1002/chem.201902206

Author

Donslund, Aske S. ; Neumann, Karoline T. ; Corneliussen, Nicklas P. ; Grove, Ebbe K. ; Herbstritt, Domenique ; Daasbjerg, Kim ; Skrydstrup, Troels. / Access to β-Ketonitriles through Nickel-Catalyzed Carbonylative Coupling of α-Bromonitriles with Alkylzinc Reagents. In: Chemistry - A European Journal. 2019 ; Vol. 25, No. 42. pp. 9856-9860.

Bibtex

@article{9a533c0cc48a45ad8b6844499f2f4f7f,
title = "Access to β-Ketonitriles through Nickel-Catalyzed Carbonylative Coupling of α-Bromonitriles with Alkylzinc Reagents",
abstract = "Herein, we report a nickel-catalyzed carbonylative coupling of α-bromonitriles and alkylzinc reagents with near stoichiometric carbon monoxide to give β-ketonitriles in good yields. The reaction is catalyzed by a readily available and stable nickel(II) pincer complex. The developed protocol tolerates substrates bearing a variety of functional groups, which would be problematic or incompatible with previous synthetic methods. Additionally, we demonstrate the suitability of the method for carbon isotope labeling by the synthesis of 13C-labeled β-ketonitriles and their transformation into isotopically labeled heterocycles.",
keywords = "alkylzinc reagents, beta-ketonitriles, carbonylation, isotope labeling, nickel catalysis, BIMETALLIC OXIDATIVE ADDITION, BENZOYLACETONITRILES, METALATED NITRILES, IMINES, ARYLATION, EFFICIENT SYNTHESIS, KETONES, ORGANIC HALIDES, EXCHANGE, OXONITRILES",
author = "Donslund, {Aske S.} and Neumann, {Karoline T.} and Corneliussen, {Nicklas P.} and Grove, {Ebbe K.} and Domenique Herbstritt and Kim Daasbjerg and Troels Skrydstrup",
year = "2019",
month = jul,
doi = "10.1002/chem.201902206",
language = "English",
volume = "25",
pages = "9856--9860",
journal = "Chemistry: A European Journal",
issn = "0947-6539",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "42",

}

RIS

TY - JOUR

T1 - Access to β-Ketonitriles through Nickel-Catalyzed Carbonylative Coupling of α-Bromonitriles with Alkylzinc Reagents

AU - Donslund, Aske S.

AU - Neumann, Karoline T.

AU - Corneliussen, Nicklas P.

AU - Grove, Ebbe K.

AU - Herbstritt, Domenique

AU - Daasbjerg, Kim

AU - Skrydstrup, Troels

PY - 2019/7

Y1 - 2019/7

N2 - Herein, we report a nickel-catalyzed carbonylative coupling of α-bromonitriles and alkylzinc reagents with near stoichiometric carbon monoxide to give β-ketonitriles in good yields. The reaction is catalyzed by a readily available and stable nickel(II) pincer complex. The developed protocol tolerates substrates bearing a variety of functional groups, which would be problematic or incompatible with previous synthetic methods. Additionally, we demonstrate the suitability of the method for carbon isotope labeling by the synthesis of 13C-labeled β-ketonitriles and their transformation into isotopically labeled heterocycles.

AB - Herein, we report a nickel-catalyzed carbonylative coupling of α-bromonitriles and alkylzinc reagents with near stoichiometric carbon monoxide to give β-ketonitriles in good yields. The reaction is catalyzed by a readily available and stable nickel(II) pincer complex. The developed protocol tolerates substrates bearing a variety of functional groups, which would be problematic or incompatible with previous synthetic methods. Additionally, we demonstrate the suitability of the method for carbon isotope labeling by the synthesis of 13C-labeled β-ketonitriles and their transformation into isotopically labeled heterocycles.

KW - alkylzinc reagents

KW - beta-ketonitriles

KW - carbonylation

KW - isotope labeling

KW - nickel catalysis

KW - BIMETALLIC OXIDATIVE ADDITION

KW - BENZOYLACETONITRILES

KW - METALATED NITRILES

KW - IMINES

KW - ARYLATION

KW - EFFICIENT SYNTHESIS

KW - KETONES

KW - ORGANIC HALIDES

KW - EXCHANGE

KW - OXONITRILES

UR - http://www.scopus.com/inward/record.url?scp=85068413625&partnerID=8YFLogxK

U2 - 10.1002/chem.201902206

DO - 10.1002/chem.201902206

M3 - Journal article

C2 - 31162751

AN - SCOPUS:85068413625

VL - 25

SP - 9856

EP - 9860

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

SN - 0947-6539

IS - 42

ER -