Catalyst‐free Chloroamination Cyclization Cascade with Sodium Hypochlorite: from N‐(Pentenyl)sulfonylamides to 2‐(1‐Chloromethyl)pyrrolidines

A mild and catalyst‐free protocol to obtain several 2‐chloromethylpyrrolidines by the use of a commercial solution of sodium hypochlorite is here reported, without the need for a light source. The choice of the solvent revealed to be crucial in the success of the reaction. Mechanistic studies, both...

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Bibliographic Details
Published in:European journal of organic chemistry 2024-06, Vol.27 (21), p.n/a
Main Authors: Scarfiello, Jacopo, Rusconi, Marco, Lanfranco, Alberto, Azzi, Emanuele, Caracciolo, Stefano, Ghigo, Giovanni, Renzi, Polyssena, Deagostino, Annamaria
Format: Article
Language:English
Subjects:
catalyst free
Catalysts
Chlorine
chloroamination
domino reaction
hypochlorite
Light sources
Oxidation
Oxidizing agents
pyrrolidines
sodium
Sodium hypochlorite
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Summary:A mild and catalyst‐free protocol to obtain several 2‐chloromethylpyrrolidines by the use of a commercial solution of sodium hypochlorite is here reported, without the need for a light source. The choice of the solvent revealed to be crucial in the success of the reaction. Mechanistic studies, both experimental and computational, confirmed a radical mechanism, where the deprotonation step, followed by the oxidation of a N‐centered anion to the corresponding radical, allowed 2‐chloromethylpyrrolidines, by a very fast cyclization, to be obtained. Sodium hypochlorite plays the role of both the oxidant and the chlorine source. No catalyst is needed to cyclize a sulfonylated aminoalkene in the presence of commercial sodium hypochlorite, a catalytic amount of a base in tetrahydrofuran (THF), thus obtaining valuable 2‐chloromethylpyrrolidines via a domino process and a key nitrogen‐centered radical
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400108