Skip navigation

Expedient access to cyanated N-Heterocycles via direct flow-electrochemical C(sp2)-H activation

Expedient access to cyanated N-Heterocycles via direct flow-electrochemical C(sp2)-H activation

Carvalho, Mary-Ambre, Demin, Samuël, Martinez-Lamenca, Carolina, Romanov-Michailidis, Fedor, Lam, Kevin ORCID: 0000-0003-1481-9212, Rombouts, Frederik and Lecomte, Morgan (2021) Expedient access to cyanated N-Heterocycles via direct flow-electrochemical C(sp2)-H activation. Chemistry - A European Journal. ISSN 0947-6539 (Print), 1521-3765 (Online) (doi:https://doi.org/10.1002/chem.202103384)

[img] PDF (Author's accepted manuscript (AAM))
34197_LAM-_Expedient_access_to_cyanated .pdf - Accepted Version
Restricted to Repository staff only until 19 October 2022.
Available under License Creative Commons Attribution Non-commercial No Derivatives.

Download (830kB) | Request a copy

Abstract

Nitriles are recurring motifs in bioactive molecules and versatile functional groups in synthetic chemistry. Despite recent progress, direct introduction of a nitrile moiety in heteroarenes remains challenging. Recent developments in electrochemical reactions pave the way to more practical cyanation protocols. However, currently available methods typically require hazardous cyanide sources, expensive mediators, and often suffer from narrow substrate scope and laborious reaction set-up. To address the limitations of current synthetic methods, we report here an effective, sustainable, and scalable procedure for the direct C(sp2)-H cyanation of aromatic N-heterocycles with a user-friendly flow-electrochemical set-up. Furthermore, high substrate and functional group tolerance is demonstrated, allowing for late-stage functionalization of drug-like scaffolds such as natural products and pharmaceuticals.

Item Type: Article
Uncontrolled Keywords: electrosynthesis, cyanation, radicals, flow
Subjects: Q Science > QD Chemistry
Faculty / School / Research Centre / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > School of Science (SCI)
Related URLs:
Last Modified: 20 Oct 2021 09:41
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
Selected for GREAT 2019: None
Selected for REF2021: None
URI: http://gala.gre.ac.uk/id/eprint/34197

Actions (login required)

View Item View Item

Downloads

Downloads per month over past year

View more statistics