A New Portal to SuFEx Click Chemistry: A Stable Fluorosulfuryl Imidazolium Salt Emerging as an "F-SO2+" Donor of Unprecedented Reactivity, Selectivity, and Scope

被引：167

作者：

Guo, Taijie ^{[1
]}

Meng, Genyi ^{[1
]}

Zhan, Xiongjie ^{[1
]}

Yang, Qian ^{[2
]}

Ma, Tiancheng ^{[1
]}

Xu, Long ^{[1
]}

Sharpless, K. Barry ^{[1
]}

Dong, Jiajia ^{[1
]}

机构：

[1] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Chinese Acad Sci, Key Lab Organofluorine Chem,Ctr Excellence Mol Sy, 345 Ling Ling Rd, Shanghai 200032, Peoples R China

[2] 187 Bldg,1799 Yinchun Rd, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 10期

基金：

中国国家自然科学基金;

关键词：

azolium salts; click chemistry; fluorosulfurylation; SuFEx chemistry; sulfamoyl fluoride; SULFUR(VI) FLUORIDE EXCHANGE; ARYL FLUOROSULFATES; SULFONYL FLUORIDES; TRANSTHYRETIN; INHIBITORS; EFFICIENT; PROTEINS; STRATEGY; PHENOLS; SURFACE;

D O I：

10.1002/anie.201712429

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Sulfuryl fluoride, SO2F2, has been found to derivatize phenols in all kinds of environments, even those in highly functional molecules. We now report that a solid fluorosulfuryl imidazolium triflate salt delivers the same F-SO2+ fragment to Nu-H acceptor groups in the substrates. However, this triflate salt is a far more reactive fluorosulfurylating agent than SO2F2 and displays selectivity preferences of its own. Moreover, the new azolium triflate reagent reacts once with primary amines and anilines before the reaction stops. On the other hand, with triethylamine and two equivalents of the F-SO2+ donor present, it proceeds on to the bis(fluorosulfuryl)imides in good yieldtwo important conversions that we have never seen with sulfuryl fluoride as the electrophile.

引用

页码：2605 / 2610

页数：6

共 55 条

[1] Potential peptidic proteasome inhibitors by incorporation of an electrophilic trap based on amino acid derived α-substituted sulfonyl fluorides [J].

Alvarez, Natalia Herrero ;

van de langemheen, Helmus ;

Brouwer, Arwin J. ;

Liskamp, Rob M. J. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (19) :5055-5063

[2]

[Anonymous], 2002, DOW AGROSCIENCES TEC

[3] A Fluorogenic Aryl Fluorosulfate for Intraorganellar Transthyretin Imaging in Living Cells and in Caenorhabditis elegans [J].

Baranczak, Aleksandra ;

Liu, Yu ;

Connelly, Stephen ;

Du, Wen-Ge Han ;

Greiner, Erin R. ;

Genereux, Joseph C. ;

Wiseman, R. Luke ;

Eisele, Yvonne S. ;

Bradbury, Nadine C. ;

Dong, Jiajia ;

Noodleman, Louis ;

Sharpless, K. Barry ;

Wilson, Ian A. ;

Encalada, Sandra E. ;

Kelly, Jeffery W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (23) :7404-7414

[4] Preparation of unsymmetrical sulfonylureas from N,N′-sulfuryldiimidazoles [J].

Beaudoin, S ;

Kinsey, KE ;

Burns, JF .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (01) :115-119

[5] SuFEx - a selectively triggered chemistry for fast, efficient and equimolar polymer-polymer coupling reactions [J].

Brendel, Johannes C. ;

Martin, Liam ;

Zhang, Junliang ;

Perrier, Sebastien .

POLYMER CHEMISTRY, 2017, 8 (48) :7475-7485

[6] Multifunctional Surface Manipulation Using Orthogonal Click Chemistry [J].

Brooks, Karson ;

Yatvin, Jeremy ;

McNitt, Christopher D. ;

Reese, R. Alexander ;

Jung, Calvin ;

Popik, Vladimir V. ;

Locklin, Jason .

LANGMUIR, 2016, 32 (26) :6600-6605

[7] Development and Application of O-(Trimethylsilyl)aryl Fluorosulfates for the Synthesis of Arynes [J].

Chen, Qiao ;

Yu, Hongmei ;

Xu, Zhaoqing ;

Lin, Li ;

Jiang, Xianxing ;

Wang, Rui .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (13) :6890-6896

[8]

Chen W., 2015, Angew. Chem. Int. Ed, V128, P1867, DOI DOI 10.1002/ANGE.201509016

[9] Arylfluorosulfates Inactivate Intracellular Lipid Binding Protein(s) through Chemoselective SuFEx Reaction with a Binding Site Tyr Residue [J].

Chen, Wentao ;

Dong, Jiajia ;

Plate, Lars ;

Mortenson, David E. ;

Brighty, Gabriel J. ;

Li, Suhua ;

Liu, Yu ;

Galmozzi, Andrea ;

Lee, Peter S. ;

Hulce, Jonathan J. ;

Cravatt, Benjamin F. ;

Saez, Enrique ;

Powers, Evan T. ;

Wilson, Ian A. ;

Sharpless, K. Barry ;

Kelly, Jeffery W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (23) :7353-7364

[10] Synthesis of Sulfotyrosine-Containing Peptides by Incorporating Fluorosulfated Tyrosine Using an Fmoc-Based Solid-Phase Strategy [J].

Chen, Wentao ;

Dong, Jiajia ;

Li, Suhua ;

Liu, Yu ;

Wang, Yujia ;

Yoon, Leonard ;

Wu, Peng ;

Sharpless, K. Barry ;

Kelly, Jeffery W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (05) :1835-1838

← 1 2 3 4 5 6 →