Bellesia, Franco, Clark, Andrew J., Felluga, Fulvia, Gennaro, Armando, Isse, Abdirisak A., Roncaglia, Fabrizio and Ghelfi, Franco (2013) Efficient and green route to γ-Lactams by copper-catalysed reversed atom transfer radical cyclisation of α-polychloro-N-allylamides, using a low load of metal (0.5 mol%). Advanced Synthesis & Catalysis, Volume 355 (Number 8). pp. 1649-1660. doi:10.1002/adsc.201300132 ISSN 1615-4150.

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Abstract

The cyclisation of N-allyl-N-substituted-α-polychloroamides is efficiently obtained through a copper-catalysed activators regenerated by electron transfer–atom transfer radical cyclisation process, with a metal load of only 0.5 mol%. The redox catalyst is introduced in its inactive form as copper(II) chloride/[nitrogen ligand] complex, and continuously regenerated to the active copper(I) chloride/[nitrogen ligand] species by ascorbic acid. To preserve the catalyst integrity, the hydrochloric acid, released after each regeneration cycle, has been quenched by carbonate. The choice of the solvent is critical, the best performance being observed in ethyl acetate-ethanol (3:1).

Item Type:	Journal Article
Divisions:	Faculty of Science, Engineering and Medicine > Science > Chemistry
Journal or Publication Title:	Advanced Synthesis & Catalysis
Publisher:	Wiley-VCH Verlag GMBH
ISSN:	1615-4150
Official Date:	2013
Dates:	Date Event 2013 Published
Volume:	Volume 355
Number:	Number 8
Page Range:	pp. 1649-1660
DOI:	10.1002/adsc.201300132
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access

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