Site-selective 18F fluorination of unactivated C-H bonds mediated by a manganese porphyrin

Wei Liu; Xiongyi Huang; Michael S. Placzek; Shane W. Krska; Paul McQuade; Jacob M. Hooker; John Taylor Groves

doi:10.1039/c7sc04545j

Site-selective ¹⁸F fluorination of unactivated C-H bonds mediated by a manganese porphyrin

Wei Liu, Xiongyi Huang, Michael S. Placzek, Shane W. Krska, Paul McQuade, Jacob M. Hooker, John Taylor Groves

Research output: Contribution to journal › Article › peer-review

70 Scopus citations

Abstract

The first direct C-H ¹⁸F fluorination reaction of unactivated aliphatic sites using no-carrier-Added [¹⁸F]fluoride is reported. Under the influence of a manganese porphyrin/iodosylbenzene system, a variety of unactivated aliphatic C-H bonds can be selectively converted to C-¹⁸F bonds. The mild conditions, broad substrate scope and generally inaccessible regiochemistry make this radio-fluorination a powerful alternate to established nucleophilic substitution for the preparation of ¹⁸F labeled radio tracers.

Original language	English (US)
Pages (from-to)	1168-1172
Number of pages	5
Journal	Chemical Science
Volume	9
Issue number	5
DOIs	https://doi.org/10.1039/c7sc04545j
State	Published - 2018

All Science Journal Classification (ASJC) codes

General Chemistry

Access to Document

10.1039/c7sc04545j

Cite this

@article{446680aabbc4487a9da2797ed3549e24,

title = "Site-selective 18F fluorination of unactivated C-H bonds mediated by a manganese porphyrin",

abstract = "The first direct C-H 18F fluorination reaction of unactivated aliphatic sites using no-carrier-Added [18F]fluoride is reported. Under the influence of a manganese porphyrin/iodosylbenzene system, a variety of unactivated aliphatic C-H bonds can be selectively converted to C-18F bonds. The mild conditions, broad substrate scope and generally inaccessible regiochemistry make this radio-fluorination a powerful alternate to established nucleophilic substitution for the preparation of 18F labeled radio tracers.",

author = "Wei Liu and Xiongyi Huang and Placzek, {Michael S.} and Krska, {Shane W.} and Paul McQuade and Hooker, {Jacob M.} and Groves, {John Taylor}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2018.",

year = "2018",

doi = "10.1039/c7sc04545j",

language = "English (US)",

volume = "9",

pages = "1168--1172",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

number = "5",

}

TY - JOUR

T1 - Site-selective 18F fluorination of unactivated C-H bonds mediated by a manganese porphyrin

AU - Liu, Wei

AU - Huang, Xiongyi

AU - Placzek, Michael S.

AU - Krska, Shane W.

AU - McQuade, Paul

AU - Hooker, Jacob M.

AU - Groves, John Taylor

N1 - Publisher Copyright: © The Royal Society of Chemistry 2018.

PY - 2018

Y1 - 2018

N2 - The first direct C-H 18F fluorination reaction of unactivated aliphatic sites using no-carrier-Added [18F]fluoride is reported. Under the influence of a manganese porphyrin/iodosylbenzene system, a variety of unactivated aliphatic C-H bonds can be selectively converted to C-18F bonds. The mild conditions, broad substrate scope and generally inaccessible regiochemistry make this radio-fluorination a powerful alternate to established nucleophilic substitution for the preparation of 18F labeled radio tracers.

AB - The first direct C-H 18F fluorination reaction of unactivated aliphatic sites using no-carrier-Added [18F]fluoride is reported. Under the influence of a manganese porphyrin/iodosylbenzene system, a variety of unactivated aliphatic C-H bonds can be selectively converted to C-18F bonds. The mild conditions, broad substrate scope and generally inaccessible regiochemistry make this radio-fluorination a powerful alternate to established nucleophilic substitution for the preparation of 18F labeled radio tracers.

UR - http://www.scopus.com/inward/record.url?scp=85041451877&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85041451877&partnerID=8YFLogxK

U2 - 10.1039/c7sc04545j

DO - 10.1039/c7sc04545j

M3 - Article

C2 - 29675161

AN - SCOPUS:85041451877

SN - 2041-6520

VL - 9

SP - 1168

EP - 1172

JO - Chemical Science

JF - Chemical Science

IS - 5

ER -

Site-selective ¹⁸F fluorination of unactivated C-H bonds mediated by a manganese porphyrin

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this