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Cu0-promoted cyclisation of unsaturated α-halogeno amides to give β- and γ-Lactams
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Clark, Andrew J., Duckmanton, Jonathan N., Felluga, Fulvia, Gennaro, Armando, Ghelfi, Franco, Hardiman, Jack R. D., Isse, Abdirisak A., Manferdini, Claudia and Spinelli, Domenico (2016) Cu0-promoted cyclisation of unsaturated α-halogeno amides to give β- and γ-Lactams. European Journal of Organic Chemistry, 2016 (14). pp. 2479-2491. doi:10.1002/ejoc.201600249 ISSN 1434-193X.
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WRAP_9370232-ch-060516-sara-atrc_manuscript_eujoc_ajclark_corrections1.pdf - Accepted Version Embargoed item. Restricted access to Repository staff only - Requires a PDF viewer. Download (354Kb) |
Official URL: http://dx.doi.org/10.1002/ejoc.201600249
Abstract
Efficient 5-exo-trig atom-transfer radical cyclisation of 13 unsaturated α-halogeno amides mediated by Cu0 (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 Cu0 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 β-lactams, although these reactions gave lower yields (35–76 %).
Item Type: | Journal Article | ||||||||||
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Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||||
Journal or Publication Title: | European Journal of Organic Chemistry | ||||||||||
Publisher: | Wiley | ||||||||||
ISSN: | 1434-193X | ||||||||||
Official Date: | May 2016 | ||||||||||
Dates: |
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Volume: | 2016 | ||||||||||
Number: | 14 | ||||||||||
Page Range: | pp. 2479-2491 | ||||||||||
DOI: | 10.1002/ejoc.201600249 | ||||||||||
Status: | Peer Reviewed | ||||||||||
Publication Status: | Published | ||||||||||
Access rights to Published version: | Restricted or Subscription Access | ||||||||||
Date of first compliant deposit: | 9 May 2016 |
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