The cyclisation of N-allyl-N-substituteda- 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).

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%) / Bellesia, Franco; Andrew J., Clark; Fulvia, Felluga; Armando, Gennaro; Abdirisak A., Isse; Roncaglia, Fabrizio; Ghelfi, Franco. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - STAMPA. - 355:(2013), pp. 1649-1660. [10.1002/adsc.201300132]

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%)

BELLESIA, Franco;RONCAGLIA, Fabrizio;GHELFI, Franco
2013-01-01

Abstract

The cyclisation of N-allyl-N-substituteda- 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).
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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%) / Bellesia, Franco; Andrew J., Clark; Fulvia, Felluga; Armando, Gennaro; Abdirisak A., Isse; Roncaglia, Fabrizio; Ghelfi, Franco. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - STAMPA. - 355:(2013), pp. 1649-1660. [10.1002/adsc.201300132]
Bellesia, Franco; Andrew J., Clark; Fulvia, Felluga; Armando, Gennaro; Abdirisak A., Isse; Roncaglia, Fabrizio; Ghelfi, Franco
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/963698
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