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

Clark, Andrew J
•
Duckmanton, Jonathan N.
•
FELLUGA, FULVIA
altro
Spinelli, Domenico
2016
  • journal article

Periodico
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
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 %).
DOI
10.1002/ejoc.201600249
WOS
WOS:000377250900015
Archivio
http://hdl.handle.net/11368/2877014
info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-84964670232
http://dx.doi.org/10.1002/ejoc.201600249
Diritti
closed access
license:digital rights management non definito
license:digital rights management non definito
FVG url
https://arts.units.it/request-item?handle=11368/2877014
Soggetti
  • Copper

  • Cyclization

  • Homogeneous catalysi

  • Nitrogen heterocycle

  • Radical reaction

  • Redox chemistry

  • Organic Chemistry

  • Physical and Theoreti...

Web of Science© citazioni
5
Data di acquisizione
Mar 28, 2024
Visualizzazioni
1
Data di acquisizione
Apr 19, 2024
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