Friedel–Crafts-Type Electrophilic Radiocyanation of (Hetero)arenes

Organic Letters 2026 Open access

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Authors: Casey J. McCarthy, Martie Muller, Richard Ma, Umberto Maria Battisti, Jay S. Wright, E William Webb, Melanie Sarah Sanford, Matthias M. Herth, Peter J. H. Scott
DOI: 10.1021/acs.orglett.6c00078
Cited by: 1
References: 44

Abstract

Radiocyanation is an attractive approach to introduce carbon-11 into radiopharmaceuticals, as nitriles and other acyl moieties. This report describes a Friedel–Crafts-type electrophilic radiocyanation of (hetero)aryltrimethylgermanes and trimethylstannanes as well as a direct C–H radiocyanation of (hetero)arenes. This approach leverages the in situ oxidation of [ 11 C]CN – to [ 11 C]CNCl to enable electrophilic aromatic substitution pathways for accessing relevant 11 C-aryl nitrile scaffolds. This method proceeds in short reaction times with readily available, shelf-stable reagents and enables radiocyanation of diverse substrates in good radiochemical yields.

Fields of Study & Subjects

Catalytic C–H Functionalization Methods Chemical Reactions and Isotopes Advanced Synthetic Organic Chemistry

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
7
Pages
2421–2426
Publication date
9 February 2026
Language
EN