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eCyanation using 5‑Aminotetrazole as a safer electrophilic and nucleophilic cyanide source

eCyanation using 5‑Aminotetrazole as a safer electrophilic and nucleophilic cyanide source

Morlacci, Valerio, Milia, Marco, Saiter, Jérémy, Preet Bhela, Irene, Leech, Matthew C. and Lam, Kevin ORCID: 0000-0003-1481-9212 (2024) eCyanation using 5‑Aminotetrazole as a safer electrophilic and nucleophilic cyanide source. Journal of the American Chemical Society AU. ISSN 2691-3704 (Online) (doi:https://doi.org/10.1021/jacsau.4c00768)

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48460 LAM_eCyanation_Using_5‑Aminotetrazole_As_A_Safer_Electrophilic_And_Nucleophilic_Cyanide_Source_(OA)_2024.pdf - Published Version
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Abstract

An electrochemical method for carrying out safercyanation reactions is reported. The use of 5-aminotetrazole as acyanide source enabled the successful electrogeneration of bothelectrophilic and nucleophilic cyanide sources. To demonstrate theversatility of the method, a variety of cyanation reactions werecarried out, including the synthesis of cyanamides, N-heterocycles,and aromatic nitriles, as well as the nucleophilic addition ofcyanides to a variety of electrophiles without the need to handlehighly toxic cyanide salts. Finally, as a proof of concept forscalability, the cyanation methodology was rapidly transferred to aflow electrosynthesis setup, which demonstrated its potential forlarge-scale applications

Item Type: Article
Uncontrolled Keywords: cyanation reaction, electrochemical cyanation, anodic oxidation, electrosynthesis, flow chemistry, cyanogen bromide, cyanide source
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
T Technology > TK Electrical engineering. Electronics Nuclear engineering
Faculty / School / Research Centre / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > School of Science (SCI)
Last Modified: 07 Nov 2024 12:15
URI: http://gala.gre.ac.uk/id/eprint/48460

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