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Synthesis of Arylidene-β-lactams via exo-Selective Matsuda-Heck Arylation of Methylene-β-lactams

Nastja Riemer, Martin Riemer, Mandy Krüger, Guy J. Clarkson, Michael Shipman* and Bernd Schmidt*

*University of Warwick, Gibbet Hill Road, Coventry CV4 7AL, U.K.; Universitaet Potsdam, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam, Germany, Email: m.shipmanwarwick.ac.uk, bernd.schmidtuni-potsdam.de

N. Riemer, M. Riemer, M. Krüger, G. J. Clarkson, M. Shipman, B. Schmidt, J. Org. Chem., 2021, 86, 8786-8796.

DOI: 10.1021/acs.joc.1c00638 (free Supporting Information)



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Abstract

exo-Methylene-β-lactams were synthesized in two steps from commercially available 3-bromo-2-(bromomethyl)propionic acid and reacted with arene diazonium salts in a Heck-type arylation with high exo- and E-selectivity in the presence of catalytic amounts of Pd(OAc)2 under ligand-free conditions. The reaction provides arylidene-β-lactams in high yields as single isomers.

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Key Words

Heck reaction, β-lactams


ID: J42-Y2021