Development of fluorination methods using continuous-flow microreactors

作者: Marcus Baumann , Ian R. Baxendale , Laetitia J. Martin , Steven V. Ley

DOI: 10.1016/J.TET.2009.05.083

关键词: TrifluoromethylationNucleophileElectrophilic fluorinationDiethylaminosulfur trifluorideContinuous flowChemistryMicroreactorOrganic chemistryElectrophileReagent

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

参考文章(73)
Andreas Kirschning, Wladimir Solodenko, Klaas Mennecke, Combining enabling techniques in organic synthesis: continuous flow processes with heterogenized catalysts. Chemistry: A European Journal. ,vol. 12, pp. 5972- 5990 ,(2006) , 10.1002/CHEM.200600236
R. Eric Banks, Suad N. Mohialdin-Khaffaf, G. Sankar Lal, Iqbal Sharif, Robert G. Syvret, 1-Alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts: a novel family of electrophilic fluorinating agents Journal of The Chemical Society, Chemical Communications. pp. 595- 596 ,(1992) , 10.1039/C39920000595
Catherine J. Smith, Francisco Javier Iglesias-Sigüenza, Ian R. Baxendale, Steven V. Ley, Flow and batch mode focused microwave synthesis of 5-amino-4-cyanopyrazoles and their further conversion to 4-aminopyrazolopyrimidines. Organic and Biomolecular Chemistry. ,vol. 5, pp. 2758- 2761 ,(2007) , 10.1039/B709043A
Harold F. Hodson, David J. Madge, Alexandra N.Z. Slawin, David A. Widdowson, David J. Williams, Electrophilic fluorination in the synthesis of new fluoroindoles Tetrahedron. ,vol. 50, pp. 1899- 1906 ,(1994) , 10.1016/S0040-4020(01)80862-0
Kenneth Kirk, Selective Fluorination in Drug Design and Development: An Overview of Biochemical Rationales Current Topics in Medicinal Chemistry. ,vol. 6, pp. 1447- 1456 ,(2006) , 10.2174/156802606777951073
C.W. Buss, P.L. Coe, J.C. Tatlow, 3,3-Difluorochlorambucil Journal of Fluorine Chemistry. ,vol. 34, pp. 83- 104 ,(1986) , 10.1016/S0022-1139(00)81929-6