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

Casey J McCarthy; Marius Müller; Richard Ma; Umberto Maria Battisti; Jay S Wright; E William Webb; Melanie S Sanford; Matthias M Herth; Peter J H Scott

doi:10.1021/acs.orglett.6c00078

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

Casey J McCarthy, Marius Müller, Richard Ma, Umberto Maria Battisti, Jay S Wright, E William Webb, Melanie S Sanford, Matthias M Herth^*, Peter J H Scott

^*Corresponding author af dette arbejde

Afdeling for Klinisk Fysiologi og Nuklearmedicin DIA

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 [11C]CN- to [11C]CNCl to enable electrophilic aromatic substitution pathways for accessing relevant 11C-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.

Originalsprog	Engelsk
Tidsskrift	Organic letters
Sider (fra-til)	2421-2426
Antal sider	6
ISSN	1523-7052
DOI	https://doi.org/10.1021/acs.orglett.6c00078
Status	E-pub ahead of print - 9 feb. 2026

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10.1021/acs.orglett.6c00078

Citationsformater

@article{315f16079314453cb57c56d430e83594,

title = "Friedel-Crafts-Type Electrophilic Radiocyanation of (Hetero)arenes",

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 [11C]CN- to [11C]CNCl to enable electrophilic aromatic substitution pathways for accessing relevant 11C-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.",

author = "McCarthy, \{Casey J\} and Marius M{\"u}ller and Richard Ma and Battisti, \{Umberto Maria\} and Wright, \{Jay S\} and Webb, \{E William\} and Sanford, \{Melanie S\} and Herth, \{Matthias M\} and Scott, \{Peter J H\}",

year = "2026",

month = feb,

day = "9",

doi = "10.1021/acs.orglett.6c00078",

language = "English",

pages = "2421--2426",

journal = "Organic letters",

issn = "1523-7052",

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TY - JOUR

T1 - Friedel-Crafts-Type Electrophilic Radiocyanation of (Hetero)arenes

AU - McCarthy, Casey J

AU - Müller, Marius

AU - Ma, Richard

AU - Battisti, Umberto Maria

AU - Wright, Jay S

AU - Webb, E William

AU - Sanford, Melanie S

AU - Herth, Matthias M

AU - Scott, Peter J H

PY - 2026/2/9

Y1 - 2026/2/9

N2 - 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 [11C]CN- to [11C]CNCl to enable electrophilic aromatic substitution pathways for accessing relevant 11C-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.

AB - 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 [11C]CN- to [11C]CNCl to enable electrophilic aromatic substitution pathways for accessing relevant 11C-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.

U2 - 10.1021/acs.orglett.6c00078

DO - 10.1021/acs.orglett.6c00078

M3 - Letter

C2 - 41661077

SN - 1523-7052

SP - 2421

EP - 2426

JO - Organic letters

JF - Organic letters

ER -

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

Abstract

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