Silver-catalyzed radical carbofluorination of unactivated alkenes with acetic acid in aqueous solution

被引：39

作者：

Chen, He ^{[1
,2
]}

Zhu, Lin ^{[1
,2
]}

Li, Chaozhong ^{[1
,2
,3
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Collaborat Innovat Ctr Chem Life Sci, 345 Lingling Rd, Shanghai 200032, Peoples R China

[3] Ningbo Univ Technol, Sch Chem Engn, 89 Cuibai Rd, Ningbo 315016, Zhejiang, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 04期

基金：

中国国家自然科学基金;

关键词：

FLUORINATION; STYRENES; FLUOROARYLATION; LACTONES; MEDIA;

D O I：

10.1039/c6qo00854b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The AgNO3-catalyzed reactions of unactivated alkenes with acetic acid and Selectfluor reagent in aqueous solution afforded the corresponding gamma-fluorinated carboxylic acids under mild conditions. Carbofluorination was not only efficient and regioselective, but also enjoyed a wide functional group compatibility.

引用

页码：565 / 568

页数：4

共 35 条

[1] 1-ALKYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE SALTS - A NOVEL FAMILY OF ELECTROPHILIC FLUORINATING AGENTS [J].

BANKS, RE ;

MOHIALDINKHAFFAF, SN ;

LAL, GS ;

SHARIF, I ;

SYVRET, RG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (08) :595-596

[2]

BIRDSALL NJ, 1971, TETRAHEDRON LETT, P2675

[3] OXIDATION REACTIONS OF MANGANESE(3) ACETATE .2. FORMATION OF GAMMA-LACTONES FROM OLEFINS AND ACETIC ACID [J].

BUSH, JB ;

FINKBEIN.H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (21) :5903-&

[4] Modern Carbon-Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis [J].

Campbell, Michael G. ;

Ritter, Tobias .

CHEMICAL REVIEWS, 2015, 115 (02) :612-633

[5] Monofluorination of Organic Compounds: 10 Years of Innovation [J].

Champagne, Pier Alexandre ;

Desroches, Justine ;

Hamel, Jean-Denys ;

Vandamme, Mathilde ;

Paquin, Jean-Francois .

CHEMICAL REVIEWS, 2015, 115 (17) :9073-9174

[6] Synthesis of (2S,3S)-3′-fluoroisoleucine [J].

Charrier, JD ;

Hadfield, DS ;

Hitchcock, PB ;

Young, DW .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (05) :797-802

[7] Beyond the Balz-Schiemann Reaction: The Utility of Tetrafluoroborates and Boron Trifluoride as Nucleophilic Fluoride Sources [J].

Cresswell, Alexander J. ;

Davies, Stephen G. ;

Roberts, Paul M. ;

Thomson, James E. .

CHEMICAL REVIEWS, 2015, 115 (02) :566-611

[8] Fluorocyanation of Enamines [J].

Dilman, Alexander D. ;

Belyakov, Pavel A. ;

Struchkova, Marina I. ;

Arkhipov, Dmitry E. ;

Korlyukov, Alexander A. ;

Tartakovsky, Vladimir A. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15) :5367-5370

[9] A novel fluorinated erythromycin antibiotic [J].

Goss, RJM ;

Hong, H .

CHEMICAL COMMUNICATIONS, 2005, (31) :3983-3985

[10] Synthesis and properties of monofluorinated dimyristoylphosphatidylcholine derivatives: Potential fluorinated probes for the study of membrane topology [J].

Guimond-Tremblay, Jonathan ;

Gagnon, Marie-Claude ;

Pineault-Maltais, Jozy-Ann ;

Turcotte, Vanessa ;

Auger, Michele ;

Paquin, Jean-Francois .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (06) :1145-1148

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