Efficient 5-exo-trig atom-transfer radical cyclisation of 13 unsaturated alpha-halogeno amides mediated by Cu-0 (copper wire) with tripyridylmethanimine ligand (TPMA; 1 mol-%) in a mixed solvent of EtOAc/EtOH (3: 1) is reported (89-98 %), with recycling of the copper wire. A substantial improvement in conversion and selectivity was obtained when Na2CO3 (5 mol-%) was added to the reaction mixture. The Cu-0 acts as a supplementary activator and reducing agent in a SARA-ATRC process. The protocol was extended to the cyclisation onto alkynes and the formation of beta-lactams, although these reactions gave lower yields (35-76 %).

Cu0-Promoted Cyclisation of Unsaturated α-Halogeno Amides to Give β- And γ-Lactams

FELLUGA, FULVIA;
2016

Abstract

Efficient 5-exo-trig atom-transfer radical cyclisation of 13 unsaturated alpha-halogeno amides mediated by Cu-0 (copper wire) with tripyridylmethanimine ligand (TPMA; 1 mol-%) in a mixed solvent of EtOAc/EtOH (3: 1) is reported (89-98 %), with recycling of the copper wire. A substantial improvement in conversion and selectivity was obtained when Na2CO3 (5 mol-%) was added to the reaction mixture. The Cu-0 acts as a supplementary activator and reducing agent in a SARA-ATRC process. The protocol was extended to the cyclisation onto alkynes and the formation of beta-lactams, although these reactions gave lower yields (35-76 %).
http://dx.doi.org/10.1002/ejoc.201600249
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11368/2877014
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