Halofluorination of Alkenes Using Trihaloisocyanuric Acids and HF•Pyridine

被引：27

作者：

Crespo, Livia T. C. ^{[1
]}

Ribeiro, Rodrigo da S. ^{[1
]}

de Mattos, Marcio C. S. ^{[1
]}

Esteves, Pierre M. ^{[1
]}

机构：

[1] Univ Fed Rio de Janeiro, Dept Quim Organ, Inst Quim, BR-21945970 Rio De Janeiro, Brazil

来源：

SYNTHESIS-STUTTGART | 2010年 / 14期

关键词：

electrophilic addition; halogenation; alkenes; halides; regioselectivity; CONVENIENT REAGENT; TRICHLOROISOCYANURIC ACID; TRIIODOISOCYANURIC ACID; SYNTHETIC METHODS; BROMOFLUORINATION; FLUORINE; CHLORINATION; IODINATION; CHEMISTRY; BLOCKS;

D O I：

10.1055/s-0029-1220011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Halofluorination of alkenes with a new system (trihaloisocyanuric acids and HF center dot pyridine) results in the formation of vicinal halofluoroalkanes. The reaction is regioselective leading to Markovnikov-oriented products and the halofluorinated adducts follow anti-addition in the case of cyclohexene and 1-methylcyclohexene. Reaction yields range from 67-88%.

引用

页码：2379 / 2382

页数：4

共 37 条

[1]

ALBANESE D, 1991, GAZZ CHIM ITAL, V121, P537

[2] Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products [J].

Begue, Jean-Pierre ;

Bonnet-Delpon, Daniele .

JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (08) :992-1012

[3] 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

[4] EFFICIENT UTILIZATION OF TETRABUTYLAMMONIUM BIFLUORIDE IN HALOFLUORINATION REACTIONS [J].

CAMPS, F ;

CHAMORRO, E ;

GASOL, V ;

GUERRERO, A .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (18) :4294-4298

[5] BROMO[F-18]FLUORINATION OF CYCLOHEXENES - A METHOD FOR THE PREPARATION OF [F-18]FLUOROCYCLOHEXANES [J].

CHI, DY ;

LIDSTROM, PJ ;

CHOE, YS ;

BONASERA, TA ;

WELCH, MJ ;

KATZENELLENBOGEN, JA .

JOURNAL OF FLUORINE CHEMISTRY, 1995, 71 (01) :143-147

[6] Tribromoisocyanuric acid: A new reagent for regioselective cobromination of alkenes [J].

de Almeida, Leonardo S. ;

Esteves, Pierre M. ;

de Mattos, Marcio C. S. .

SYNLETT, 2006, (10) :1515-1518

[7] A new regioselective bromination of activated aromatic rings [J].

de Almeida, LS ;

Esteves, PM ;

de Mattos, MCS .

SYNTHESIS-STUTTGART, 2006, (02) :221-223

[8] Fluorine chemistry at the millennium [J].

Dolbier, WR .

JOURNAL OF FLUORINE CHEMISTRY, 2005, 126 (02) :157-163

[9]

DOLENC D, 1995, SYNLETT, P327

[10]

Dolenc D, 2000, SYNLETT, P544

← 1 2 3 4 →