Atom transfer radical cyclization (ATRC) of N-alkyl N-allyl dichloroamides to γ-lactams, catalyzed by 'naked' CuCl, worked efficiently in DMF, whereas, when the same dichloroamides were N-sulfonylated, DMF needed to be replaced by acetonitrile. The outcome of the cycloisomerization with N-substituted N-allyl trichloroacetamides was less affected by solvent choice, although for an effective reaction to occur, the solvent had to dissolve the cuprous salt. Catalyst loading ranged between 5 and 20 mol%.

'Ligand-free-like' CuCl-catalyzed atom transfer radical cyclization of N-substituted N-allyl polychloroamides to γ-lactams / M., Pattarozzi; Roncaglia, Fabrizio; V., Giangiordano; P., Davoli; Prati, Fabio; Ghelfi, Franco. - In: SYNTHESIS. - ISSN 0039-7881. - STAMPA. - -:4(2010), pp. 694-700. [10.1055/s-0029-1218583]

'Ligand-free-like' CuCl-catalyzed atom transfer radical cyclization of N-substituted N-allyl polychloroamides to γ-lactams.

RONCAGLIA, Fabrizio;PRATI, Fabio;GHELFI, Franco
2010

Abstract

Atom transfer radical cyclization (ATRC) of N-alkyl N-allyl dichloroamides to γ-lactams, catalyzed by 'naked' CuCl, worked efficiently in DMF, whereas, when the same dichloroamides were N-sulfonylated, DMF needed to be replaced by acetonitrile. The outcome of the cycloisomerization with N-substituted N-allyl trichloroacetamides was less affected by solvent choice, although for an effective reaction to occur, the solvent had to dissolve the cuprous salt. Catalyst loading ranged between 5 and 20 mol%.
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'Ligand-free-like' CuCl-catalyzed atom transfer radical cyclization of N-substituted N-allyl polychloroamides to γ-lactams / M., Pattarozzi; Roncaglia, Fabrizio; V., Giangiordano; P., Davoli; Prati, Fabio; Ghelfi, Franco. - In: SYNTHESIS. - ISSN 0039-7881. - STAMPA. - -:4(2010), pp. 694-700. [10.1055/s-0029-1218583]
M., Pattarozzi; Roncaglia, Fabrizio; V., Giangiordano; P., Davoli; Prati, Fabio; Ghelfi, Franco
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/645343
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