Oxidative fluorination of N-arylsulfonamides

被引：17

作者：

Buckingham, Faye ^{[1
]}

Calderwood, Samuel ^{[1
]}

Checa, Begona ^{[1
]}

Keller, Thomas ^{[1
]}

Tredwell, Matthew ^{[1
]}

Collier, Thomas Lee ^{[2
]}

Newington, Ian M. ^{[3
]}

Bhalla, Rajiv ^{[3
]}

Glaser, Matthias ^{[3
]}

Gouverneur, Veronique ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England

[2] Advion BioSyst Inc, Ithaca, NY 14850 USA

[3] Grove Ctr, GE Healthcare, Amersham HP7 9LL, England

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2015年 / 180卷

基金：

英国工程与自然科学研究理事会;

关键词：

Umpolung; Fluoride; Hypervalent iodine; F-18-radiolabelling; N-Arylsulfonamide; HYDROGEN-FLUORIDE; INHIBITORS; AGENTS; F-18; C-11;

D O I：

10.1016/j.jfluchem.2015.07.030

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

We report a late stage oxidative nucleophilic fluorination of N-arylsulfonamides, a class of compounds so far not considered as precursors to 4-fluorophenyl sulfonamides. By installing a para-positioned tertbutyl substituent on the aniline, oxidative fluorination takes place regioselectively in the presence of HF.pyridine and PIDA. This methodology has been shown to give good yields for a variety of ortho-and meta-functionalised N-arylsulfonamides and has been adapted for radiofluorination to give 4-[F-18]fluorophenyl sulfonamides under carrier added conditions. (C) 2015 Elsevier B.V. All rights reserved.

引用

收藏

页码：33 / 39

页数：7

相关论文

共 37 条

[1] Molecular imaging with PET [J].

Ametamey, Simon M. ;

Honer, Michael ;

Schubiger, Pius August .

CHEMICAL REVIEWS, 2008, 108 (05) :1501-1516

[2] Access to new 4-fluorocyclohexa-2,5-dienimines using hypervalent iodine and pyridinium polyhydrogen fluoride [J].

Basset, Lynda ;

Martin-Mingot, Agnes ;

Jouannetaud, Marie-Paule ;

Jacquesy, Jean-Claude .

TETRAHEDRON LETTERS, 2008, 49 (09) :1551-1554

[3] Synthesis of 4-fluorophenols from 4-tert-butylphenols and fluoride sources under oxidative conditions [J].

Bienvenu, A ;

Barthelemy, A ;

Boichut, S ;

Marquet, B ;

Billard, T ;

Langlois, BR .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2002, 67 (10) :1467-1478

[4] CHEMISTRY IN HYDROGEN-FLUORIDE .6. OXIDATIVE FLUORINATION OF AROMATIC-COMPOUNDS [J].

FEIRING, AE .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (08) :1252-1254

[5] Metal-Free Oxidative Fluorination of Phenols with [18F]Fluoride [J].

Gao, Zhanghua ;

Lim, Yee Hwee ;

Tredwell, Matthew ;

Li, Lei ;

Verhoog, Stefan ;

Hopkinson, Matthew ;

Kaluza, Wojciech ;

Collier, Thomas Lee ;

Passchier, Jan ;

Huiban, Mickael ;

Gouverneur, Veronique .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (27) :6733-6737

[6] Neuropharmacology and drug development [J].

Gee, AD .

BRITISH MEDICAL BULLETIN, 2003, 65 :169-177

[7] The many roles for fluorine in medicinal chemistry [J].

Hagmann, William K. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4359-4369

[8] Introduction of a hydroxy group at the para position and N-iodophenylation of N-arylamides using phenyliodine(III) bis(trifluoroacetate) [J].

Itoh, N ;

Sakamoto, T ;

Miyazawa, E ;

Kikugawa, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7424-7428

[9] A FACILE REGIOSELECTIVE AROMATIC FLUORINATION OF N-ARYL-N-HYDROXYAMIDES WITH DIETHYLAMINOSULFUR TRIFLUORIDE (DAST) [J].

KIKUGAWA, Y ;

MATSUMOTO, K ;

MITSUI, K ;

SAKAMOTO, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (12) :921-922

[10]

KOKIL PB, 1979, TETRAHEDRON LETT, P989

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