Silver-Mediated Fluorination of Functionalized Aryl Stannanes

被引：245

作者：

Furuya, Takeru ^{[1
]}

Strom, Alexandra E. ^{[1
]}

Ritter, Tobias ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 05期

关键词：

REDUCTIVE ELIMINATION; ELEMENTAL FLUORINE; ORGANIC-COMPOUNDS; CHEMISTRY; CLEAVAGE; SALTS;

D O I：

10.1021/ja8086664

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a regiospecific silver-mediated fluorination of aryl stannanes. The presented reaction can afford complex fluoroarenes from readily available phenols in three steps. The operational simplicity and the broad substrate scope of the fluorination should render this reaction a useful toot for the synthesis of milligram to gram quantities of functionalized aryl fluorides. Silver-mediated oxidative transformations of aryl nucleophiles that proceed via bimetallic redox processes are a new avenue to develop carbon-heteroatom bond formations.

引用

页码：1662 / +

页数：3

共 35 条

[1] CLEAVAGE OF ARYL-TIN BONDS WITH ELEMENTAL FLUORINE - RAPID SYNTHESIS OF [F-18] FLUOROBENZENE [J].

ADAM, MJ ;

PATE, BD ;

RUTH, TJ ;

BERRY, JM ;

HALL, LD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (15) :733-733

[2] FLUORINATION OF AROMATIC-COMPOUNDS WITH F2 AND ACETYL HYPOFLUORITE - SYNTHESIS OF F-18-ARYL FLUORIDES BY CLEAVAGE OF ARYL-TIN BONDS [J].

ADAM, MJ ;

RUTH, TJ ;

JIVAN, S ;

PATE, BD .

JOURNAL OF FLUORINE CHEMISTRY, 1984, 25 (03) :329-337

[3] Nucleophilic routes to selectively fluorinated aromatics [J].

Adams, DJ ;

Clark, JH .

CHEMICAL SOCIETY REVIEWS, 1999, 28 (04) :225-231

[4] Silver-mediated synthesis of heterocycles [J].

Alvarez-Corral, Miriam ;

Munoz-Dorado, Manuel ;

Rodirguez-Garcia, Ignacio .

CHEMICAL REVIEWS, 2008, 108 (08) :3174-3198

[5] SYNTHESIS OF ORGANOTRIALKYLSTANNANES - THE REACTION BETWEEN ORGANIC HALIDES AND HEXAALKYLDISTANNANES IN THE PRESENCE OF PALLADIUM COMPLEXES [J].

AZIZIAN, H ;

EABORN, C ;

PIDCOCK, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 215 (01) :49-58

[6] On aromatic fluoric compounds, I A new method for its representation [J].

Balz, G ;

Schiemann, G .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1927, 60 :1186-1190

[7]

BAUDOUX X, 2007, ORG REACTIONS, V69, P347

[8] SYNTHESIS AND PROPERTIES OF PHENYLSILVER [J].

BEVERWIJK, CD ;

VANDERKE.GJ .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1972, 43 (01) :C11-+

[9] Solvent effect on intramolecular hydrogen bonds in push-pull conjugated molecules [J].

Bouchy, A ;

Rinaldi, D ;

Rivail, JL .

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2004, 96 (03) :273-281

[10] SELECTIVE, ELECTROPHILIC FLUORINATIONS USING N-FLUORO-O-BENZENEDISULFONIMIDE [J].

DAVIS, FA ;

HAN, W ;

MURPHY, CK .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4730-4737

← 1 2 3 4 →