Synthesis of 4-[18F]fluorophenylalkenes and -arenes via palladium-catalyzed coupling of 4-[18F]fluoroiodobenzene with vinyl and aryl tin reagents

被引：25

作者：

Allain-Barbier, L

Lasne, MC

Perrio-Huard, C

Moreau, B

Barre, L

机构：

[1] Inst Sci Mat & Rayonnement, CNRS, UMR 6507, F-14050 Caen, France

[2] Univ Caen Basse Normandie, F-14074 Caen, France

[3] CEA, Ctr Cyceron, GDRM, F-14074 Caen, France

来源：

ACTA CHEMICA SCANDINAVICA | 1998年 / 52卷 / 04期

关键词：

D O I：

10.3891/acta.chem.scand.52-0480

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The cross-coupling reaction of 4-[F-18]fluoroiodobenzene 3a with vinyl or aryl tin reagents in the presence of tetrakis(triphenylphosphine)palladium was found to provide a convenient and rapid method for the preparation of 4-[F-18]fluorostyrene or 4-[F-18]fluorobiphenyl within 45-50 min and 47% or 86% radiochemical yields, respectively, counted from 3a. (E)-N-{3-(4-[F-18]fluorophenyl}prop-2-enyl]piperidine 2a was obtained within 45 min and in 80% radiochemical yield from 3a. 4-[F-18]Fluorobromobenzene 4a was prepared in 24-48% yield from 2-nitro-5-bromobenzaldehyde and [F-18]KF in 95 min.

引用

页码：480 / 489

页数：10

共 68 条

[1] Albertson N. F., 1962, ORG REACTIONS, V12, P157
[2] STUDIES IN TERTIARY AMINE OXIDES .2. CARBON-1O NUCLEAR MAGNETIC-RESONANCE SPECTRA OF SELECTED ACETYLENIC AMINES, THEIR N-OXIDES AND THE MEISENHEIMER REARRANGEMENT PRODUCTS
ALIRAQI, MA
ALRAWI, JMA
KHUTHIER, AH
[J]. ORGANIC MAGNETIC RESONANCE, 1980, 14 (03): : 161 - 165
[3] Allain-Barbier L., 1995, Journal of Labelled Compounds and Radiopharmaceuticals, V37, P572
[4] PALLADIUM-PROMOTED COUPLING REACTIONS OF [C-11] METHYL-IODIDE WITH ORGANOTIN AND ORGANOBORON COMPOUNDS
ANDERSSON, Y
CHENG, AP
LANGSTROM, B
[J]. ACTA CHEMICA SCANDINAVICA, 1995, 49 (09): : 683 - 688
[5] SYNTHESIS OF C-11 LABELED BENZAMIDE COMPOUNDS AS POTENTIAL TRACERS FOR POLY(ADP-RIBOSE) SYNTHETASE
ANDERSSON, Y
BERGSTROM, M
LANGSTROM, B
[J]. APPLIED RADIATION AND ISOTOPES, 1994, 45 (06) : 707 - 714
[6] SYNTHESIS OF C-11 LABELED KETONES VIA CARBONYLATIVE COUPLING REACTIONS USING [C-11] CARBON-MONOXIDE
ANDERSSON, Y
LANGSTROM, B
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (04): : 287 - 289
[7] TRANSITION METAL-MEDIATED REACTIONS USING [C-11] CYANIDE IN SYNTHESIS OF C-11 LABELED AROMATIC-COMPOUNDS
ANDERSSON, Y
LANGSTROM, B
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (11): : 1395 - 1400
[8] NUCLEOPHILIC AROMATIC-SUBSTITUTION OF ACTIVATED CATIONIC GROUPS BY F-18-LABELED FLUORIDE - A USEFUL ROUTE TO NO-CARRIER-ADDED (NCA) F-18-LABELED ARYL FLUORIDES
ANGELINI, G
SPERANZA, M
WOLF, AP
SHIUE, CY
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1985, 27 (02) : 177 - 191
[9] ANTONI G, 1992, APPL RADIAT ISOTOPES, V43, P903
[10] A NEW METHOD FOR THE NCA PRODUCTION OF [F-18] FLUOROMETHANE
BANKS, WR
SATTER, MR
HWANG, DR
[J]. APPLIED RADIATION AND ISOTOPES, 1994, 45 (01) : 69 - 74

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