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

Autor: Donslund AS; Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary, Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000, Aarhus C, Denmark., Neumann KT; Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary, Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000, Aarhus C, Denmark., Corneliussen NP; Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary, Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000, Aarhus C, Denmark., Grove EK; Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary, Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000, Aarhus C, Denmark., Herbstritt D; Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary, Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000, Aarhus C, Denmark., Daasbjerg K; Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary, Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000, Aarhus C, Denmark., Skrydstrup T; Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary, Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000, Aarhus C, Denmark.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2019 Jul 25; Vol. 25 (42), pp. 9856-9860. Date of Electronic Publication: 2019 Jul 01.
DOI: 10.1002/chem.201902206
Abstrakt: 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 13 C-labeled β-ketonitriles and their transformation into isotopically labeled heterocycles.
(© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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