Recent advances in electrophilic CF3-transfer using hypervalent iodine(III) reagents

被引：66

作者：

Kieltsch, Iris ^{[1
]}

Eisenberger, Patrick ^{[1
]}

Stanek, Kyrill ^{[1
]}

Togni, Antonio ^{[1
]}

机构：

[1] ETH, Dept Chem & Appl Biosci, Swiss Fed Inst Technol, CH-8093 Zurich, Switzerland

来源：

CHIMIA | 2008年 / 62卷 / 04期

关键词：

electrophilic trifluoromethylation; fluorinated compounds; hypervalent iodine; trifluoromethylthio ether; (trifluoromethyl)phosphine;

D O I：

10.2533/chimia.2008.260

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The development of new methodologies for an efficient introduction of CF3 groups into complex molecules constitutes one of the most challenging tasks of modern organic chemistry. Recently, we reported the access to a new class of electrophilic CF3-transfer reagents based on hypervalent iodine. The versatile application of these reagents to C-centred nucleophiles, such as beta-keto esters, silyl enol ethers and alpha-nitro esters, as well as to thiols and primary and secondary phosphines is described. Experiments with phenols afforded corresponding trifluomethylethers in very low yields.

引用

页码：260 / 263

页数：4

共 26 条

[1] CHEMISTRY OF TRIFLUOROMETHYL GROUP .4. DIPHENYLTRIFLUOROMETHYLPHOSPHINE AND COMPLEX FORMATION BY PHENYLTRIFLUOROMETHYLPHOSPHINES [J].

BEG, MAA ;

CLARK, HC .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1962, 40 (02) :283-&

[2] Synthetic uses of thio- and selenoesters of trifluoromethylated acids. 1. Preparation of trifluoromethyl sulfides and selenides [J].

Billard, T ;

Roques, N ;

Langlois, BR .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :3813-3820

[3] How to reach stereogenic trifluoromethylated carbon? En route to the "grail" of the asymmetric trifluoromethylation reaction [J].

Billard, Thierry ;

Langlois, Bernard R. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (06) :891-897

[4] Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation [J].

Eisenberger, P ;

Gischig, S ;

Togni, A .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (09) :2579-2586

[5] Mild electrophilic trifluoromethylation of secondary and primary aryl- and alkylphosphines using hypervalent iodine(III)-CF3 reagents [J].

Eisenberger, Patrick ;

Kieltsch, Iris ;

Armanino, Nicolas ;

Togni, Antonio .

CHEMICAL COMMUNICATIONS, 2008, (13) :1575-1577

[6] Substituent electronic effects in chiral ligands for asymmetric catalysis [J].

Flanagan, Susan P. ;

Guiry, Patrick J. .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (10) :2125-2154

[7] Mild electrophilic trifluoromethylation of carbon- and sulfur-centered nucleophiles by a hypervalent iodine(III)-CF3 reagent [J].

Kieltsch, Iris ;

Eisenberger, Patrick ;

Togni, Antonio .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (05) :754-757

[8]

Kukhar VP., 1995, FLUORINE CONTAINING

[9] Some recent results in nucleophilic trifluoromethylation and introduction of fluorinated moieties [J].

Langlois, BR ;

Billard, T .

SYNTHESIS-STUTTGART, 2003, (02) :185-194

[10] Mild electrophilic trifluoromethylation of β-ketoesters and silyl enol ethers with 5-trifluoro methyldibenzothiophenium tetrafluoroborate [J].

Ma, JA ;

Cahard, D .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (22) :8726-8729

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