Development of fluorination methods using continuous-flow microreactors

被引：134
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
收藏
页码：6611 / 6625
页数：15
相关论文
共 83 条
  • [1] Advanced organic synthesis using microreactor technology
    Ahmed-Omer, Batoul
    Brandt, Johan C.
    Wirth, Thomas
    [J]. 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
    BANKS, RE
    MOHIALDINKHAFFAF, SN
    LAL, GS
    SHARIF, I
    SYVRET, RG
    [J]. 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))
    BANKS, RE
    LAWRENCE, NJ
    POPPLEWELL, AL
    [J]. 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
    Baumann, Marcus
    Baxendale, Ian R.
    Ley, Steven V.
    [J]. SYNLETT, 2008, (14) : 2111 - 2114
  • [5] Azide monoliths as convenient flow reactors for efficient Curtius rearrangement reactions
    Baumann, Marcus
    Baxendale, Ian R.
    Ley, Steven V.
    Nikbin, Nikzad
    Smith, Christopher D.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (09) : 1587 - 1593
  • [6] A modular flow reactor for performing Curtius rearrangements as a continuous flow process
    Baumann, Marcus
    Baxendale, Ian R.
    Ley, Steven V.
    Nikbin, Nikzad
    Smith, Christopher D.
    Tierney, Jason P.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (09) : 1577 - 1586
  • [7] Fully automated continuous flow synthesis of 4,5-disubstituted oxazoles
    Baumann, Marcus
    Baxendale, Ian R.
    Ley, Steven V.
    Smith, Christoper D.
    Tranmer, Geoffrey K.
    [J]. 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
    Baxendale, Ian R.
    Ley, Steven V.
    Smith, Christopher D.
    Tamborini, Lucia
    Voica, Ana-Florina
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (06): : 851 - 857
  • [10] Pharmaceutical strategy and innovation: An academics perspective
    Baxendale, Ian R.
    Hayward, John J.
    Ley, Steven V.
    Tranmer, Geoffrey K.
    [J]. CHEMMEDCHEM, 2007, 2 (06) : 768 - 788
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