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%). Issue 8 (15th May 2013)

• Record Type: Journal Article
• Authors: Bellesia, Franco; Clark, Andrew J.; Felluga, Fulvia; Gennaro, Armando; Isse, Abdirisak A.; Roncaglia, Fabrizio; Ghelfi, Franco
• Is Part Of: Advanced synthesis & catalysis. Volume 355:Issue 8(2013)
• Page Start: 1649
• Page End: 1660
• Publication Date: 2013-05-15
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201300132
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The cyclisation of <italic>N</italic>‐allyl‐<italic>N</italic>‐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).</p> </abstract>