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Palladium-Catalyzed Carbonylative α-Arylation of tert-Butyl Cyanoacetate with (Hetero)aryl Bromides

Mikkel T. Jensen, Martin Juhl, Dennis U. Nielsen, Mikkel F. Jacobsen, Anders T. Lindhardt* and Troels Skrydstrup*

*Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark, Email: lindhardteng.au.dk, tschem.au.dk

M. T. Jensen, M. Juhl, D. U. Nielsen, M. F. Jacobsen, A. T. Lindhardt, T. Skrydstrup, J. Org. Chem., 2016, 81, 1358-1366.

DOI: 10.1021/acs.joc.5b02897 (free Supporting Information)


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Abstract

3-Oxo-3-(hetero)arylpropanenitriles can be synthesized via a carbonylative palladium-catalyzed α-arylation of tert-butyl 2-cyanoacetates with (hetero)aryl bromides followed by an acid-mediated decarboxylation step. Through the combination of only a stoichiometric loading of carbon monoxide and mild basic reaction conditions for the deprotonation step, an excellent functional group tolerance was ensured.

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Key Words

aryl ketones, nitriles


ID: J42-Y2016