Organic electrochemistry is a technique that allows for the heterogeneous redox reactions avoiding both the use of stoichiometric amounts of redox reagents and the resulting formation of stoichiometric by-pro- ducts. In fact, the redox reagent in these reactions is the electron, which is naturally eco-friendly and pro- duces no side compounds. It is therefore quite obvious that electrochemistry can be classified as a “green” tech- nology. The use of this methodology in the synthesis of β-lactams is not a novelty, but the growing interest in this class of biologically active compounds, due to the dis- covery of new fields of application (after a moment of decrease in interest due to antibiotic resistance) has been a stimulus for the search for more efficient electro- chemical ways to synthesize and transform β-lactams. Thus, this review deals with the twenty-first-century applications of electroorganic technique to the chemistry of β-lactams, by analyzing first the syntheses classified by the type of reactions (cyclization, cycloaddition, etc.) and then by manipulating the β-lactam structure, using it as a synthon. Lastly, the importance of this technique is demonstrated by a study of a pilot plant scale reduction of a cephalosporanic acid derivative to a commercially important antibiotic.

Organic electrochemistry: Synthesis and functionalization of β-lactams in the twenty-first century / Bortolami, Martina; Chiarotto, Isabella; Mattiello, Leonardo; Petrucci, Rita; Rocco, Daniele; Vetica, Fabrizio; Feroci, Marta. - In: HETEROCYCLIC COMMUNICATIONS. - ISSN 0793-0283. - 27:1(2021), pp. 32-44. [10.1515/hc-2020-0121]

Organic electrochemistry: Synthesis and functionalization of β-lactams in the twenty-first century

Bortolami, Martina
Membro del Collaboration Group
;
Chiarotto, Isabella
Membro del Collaboration Group
;
Mattiello, Leonardo
Membro del Collaboration Group
;
Petrucci, Rita
Membro del Collaboration Group
;
Rocco, Daniele
Membro del Collaboration Group
;
Vetica, Fabrizio
Membro del Collaboration Group
;
Feroci, Marta
2021

Abstract

Organic electrochemistry is a technique that allows for the heterogeneous redox reactions avoiding both the use of stoichiometric amounts of redox reagents and the resulting formation of stoichiometric by-pro- ducts. In fact, the redox reagent in these reactions is the electron, which is naturally eco-friendly and pro- duces no side compounds. It is therefore quite obvious that electrochemistry can be classified as a “green” tech- nology. The use of this methodology in the synthesis of β-lactams is not a novelty, but the growing interest in this class of biologically active compounds, due to the dis- covery of new fields of application (after a moment of decrease in interest due to antibiotic resistance) has been a stimulus for the search for more efficient electro- chemical ways to synthesize and transform β-lactams. Thus, this review deals with the twenty-first-century applications of electroorganic technique to the chemistry of β-lactams, by analyzing first the syntheses classified by the type of reactions (cyclization, cycloaddition, etc.) and then by manipulating the β-lactam structure, using it as a synthon. Lastly, the importance of this technique is demonstrated by a study of a pilot plant scale reduction of a cephalosporanic acid derivative to a commercially important antibiotic.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11573/1539273
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