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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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
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:	Date Event May 2016 Published 26 April 2016 Available 29 March 2016 Accepted 3 March 2016 Submitted
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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