Ring-Closing Synthesis of Dibenzothiophene Sulfonium Salts and Their Use as Leaving Groups for Aromatic 18F-Fluorination

被引：73

作者：

Gendron, Thibault ^{[1
,2
]}

Sander, Kerstin ^{[1
,2
]}

Cybulska, Klaudia ^{[2
]}

Benhamou, Laure ^{[1
,2
]}

Sin, Pak Kwan Brian ^{[1
,2
]}

Khan, Aqsa ^{[2
]}

Wood, Michael ^{[2
]}

Porter, Michael J. ^{[2
]}

Arstad, Erik ^{[1
,2
]}

机构：

[1] UCL, Inst Nucl Med, 235 Euston Rd T-5, London NW1 2BU, England

[2] UCL, Dept Chem, 20 Gordon St, London WC1H 0AJ, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 35期

基金：

英国工程与自然科学研究理事会; 英国惠康基金;

关键词：

MEDIATED F-18-FLUORINATION; PET; RADIOFLUORINATION; FLUORINATION; REARRANGEMENT; RADIOTRACER; PHENOLS;

D O I：

10.1021/jacs.8b06730

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report a novel intramolecular ring-closing reaction of biaryl thioethers that give access to highly functionalized dibenzothiophene sulfonium salts under mild conditions. The resulting precursors react regioselectively with [F-18]fluoride to give [F-18]fluoroarenes in predictable radiochemical yields. The strategy expands the available radiochemical space and provides superior labeling efficiency for clinically relevant PET tracers.

引用

页码：11125 / 11132

页数：8

共 42 条

[1]

Bernard-Gauthier Vadim, 2017, Drug Discov Today Technol, V25, P19, DOI 10.1016/j.ddtec.2017.09.001

[2] SYNTHESIS OF 4H-THIOPYRAN-4-ONES [J].

CHEN, CH ;

REYNOLDS, GA ;

VANALLAN, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (16) :2777-2778

[3] Concerted nucleophilic aromatic substitution with 19F- and 18F- [J].

Eumann, Constanze N. N. ;

Hooker, Jacob M. ;

Ritter, Tobias .

NATURE, 2016, 534 (7607) :369-373

[4] Monoamine oxidase: radiotracer chemistry and human studies [J].

Fowler, Joanna S. ;

Logan, Jean ;

Shumay, Elena ;

Alia-Klein, Nelly ;

Wang, Gene-Jack ;

Volkow, Nora D. .

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2015, 58 (03) :51-64

[5] Synthesis, characterization, and first successful monkey imaging studies of metabotropic glutamate receptor subtype 5 (mGluR5) PET radiotracers [J].

Hamill, TG ;

Krause, S ;

Ryan, C ;

Bonnefous, C ;

Govek, S ;

Seiders, TJ ;

Cosford, NDP ;

Roppe, J ;

Kamenecka, T ;

Patel, S ;

Gibson, RE ;

Sanabria, S ;

Riffel, K ;

Eng, WS ;

King, C ;

Yang, XQ ;

Green, MD ;

O'Malley, SS ;

Hargreaves, R ;

Burns, HD .

SYNAPSE, 2005, 56 (04) :205-216

[6] Synthesis of a novel oligo(p-phenylene) ladder by sulfide and sulfonio groups [J].

Haryono, A ;

Miyatake, K ;

Natori, J ;

Tsuchida, E .

MACROMOLECULES, 1999, 32 (09) :3146-3149

[7] Computational studies on hypervalent iodonium(III) compounds as activated precursors for 18F radiofluorination of electron-rich arenes [J].

Hill, David E. ;

Holland, Jason P. .

COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2015, 1066 :34-46

[8] Practical thiol surrogates and protective groups for arylthiols for Suzuki-Miyaura conditions [J].

Itoh, T ;

Mase, T .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) :2203-2206

[9] Poly(thiaheterohelicene): A stiff conjugated helical polymer comprised of fused benzothiophene rings [J].

Iwasaki, T ;

Kohinata, Y ;

Nishide, H .

ORGANIC LETTERS, 2005, 7 (05) :755-758

[10] Bi(OTf)3-, TfOH-, and TMSOTf-Mediated, One-Pot Epoxide Rearrangement, Addition, and Intramolecular Silyl-Modified Sakurai (ISMS) Cascade toward Dihydropyrans: Comparison of Catalysts and Role of Bi(OTf)3 [J].

Lambert, R. Frederick ;

Hinkle, Robert J. ;

Ammann, Stephen E. ;

Lian, Yajing ;

Liu, Jia ;

Lewis, Shane E. ;

Pike, Robert D. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (22) :9269-9277

← 1 2 3 4 5 →