Development of fluorination methods using continuous-flow microreactors

被引：135

作者：

Baumann, Marcus ^{[1
]}

Baxendale, Ian R. ^{[1
]}

Martin, Laetitia J. ^{[1
]}

Ley, Steven V. ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Innovat Technol Ctr, Cambridge CB2 1EW, England

来源：

TETRAHEDRON | 2009年 / 65卷 / 33期

基金：

英国工程与自然科学研究理事会;

关键词：

POLYMER-SUPPORTED REAGENTS; MULTISTEP ORGANIC-SYNTHESIS; DIETHYLAMINOSULFUR TRIFLUORIDE DAST; ELECTROPHILIC FLUORINATION; SELECTIVE FLUORINATION; SCAVENGERS; CHEMISTRY; CATALYSTS; REACTORS; BATCH;

D O I：

10.1016/j.tet.2009.05.083

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The safe and reliable use of various fluorination methods including nucleophilic fluorination (DAST), trifluoromethylation (Ruppert's reagent) and electrophilic fluorination (Selectfluor (R)) in a continuous-flow microreactor is reported. Special attention was given to the use of in-line scavenging procedures in order to obtain clean products without the need for further purification. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：6611 / 6625

页数：15

共 83 条

[1] Advanced organic synthesis using microreactor technology [J].

Ahmed-Omer, Batoul ;

Brandt, Johan C. ;

Wirth, Thomas .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (05) :733-740

[2] 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

[3] EFFICIENT ELECTROPHILIC FLUORINATION OF BETA-DICARBONYL COMPOUNDS WITH THE SELECTFLUOR REAGENT F-TEDA-BF4 (1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TETRAFLUOROBORATE)) [J].

BANKS, RE ;

LAWRENCE, NJ ;

POPPLEWELL, AL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (03) :343-344

[4] The use of diethylaminosulfur trifluoride (DAST) for fluorination in a continuous-flow microreactor [J].

Baumann, Marcus ;

Baxendale, Ian R. ;

Ley, Steven V. .

SYNLETT, 2008, (14) :2111-2114

[5] Azide monoliths as convenient flow reactors for efficient Curtius rearrangement reactions [J].

Baumann, Marcus ;

Baxendale, Ian R. ;

Ley, Steven V. ;

Nikbin, Nikzad ;

Smith, Christopher D. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (09) :1587-1593

[6] A modular flow reactor for performing Curtius rearrangements as a continuous flow process [J].

Baumann, Marcus ;

Baxendale, Ian R. ;

Ley, Steven V. ;

Nikbin, Nikzad ;

Smith, Christopher D. ;

Tierney, Jason P. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (09) :1577-1586

[7] Fully automated continuous flow synthesis of 4,5-disubstituted oxazoles [J].

Baumann, Marcus ;

Baxendale, Ian R. ;

Ley, Steven V. ;

Smith, Christoper D. ;

Tranmer, Geoffrey K. .

ORGANIC LETTERS, 2006, 8 (23) :5231-5234

[8]

Baxendale IR, 2007, ERNST SCHERING FOUND, V3, P151

[9] A Bifurcated Pathway to Thiazoles and Imidazoles Using a Modular Flow Microreactor [J].

Baxendale, Ian R. ;

Ley, Steven V. ;

Smith, Christopher D. ;

Tamborini, Lucia ;

Voica, Ana-Florina .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (06) :851-857

[10] Pharmaceutical strategy and innovation: An academics perspective [J].

Baxendale, Ian R. ;

Hayward, John J. ;

Ley, Steven V. ;

Tranmer, Geoffrey K. .

CHEMMEDCHEM, 2007, 2 (06) :768-788

← 1 2 3 4 5 6 7 8 9 →