Download PDF
Synlett 2008(14): 2111-2114  
DOI: 10.1055/s-2008-1078026
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

The Use of Diethylaminosulfur Trifluoride (DAST) for Fluorination in a Continuous-Flow Microreactor

Marcus Baumann, Ian R. Baxendale, Steven V. Ley*
Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK
Fax: +44(1223)336442; e-Mail: svl1000@cam.ac.uk;
Further Information

Publication History

Received 8 July 2008
Publication Date:
05 August 2008 (online)

    Permissions and Reprints All articles of this category

Abstract

The convenient and safe use of diethylaminosulfur tri­fluoride as a fluorinating agent in a continuous-flow microreactor is described using an in-line purification method to obtain clean reaction products.

Key words

microreactor - flow chemistry - immobilized reagents - fluorination - DAST

    References and Notes

  • 1a Kirk KL. Org. Process Res. Dev.  2008,  12:  305 
    Search in Google Scholar
  • 1b Kirk KL. Curr. Top. Med. Chem.  2006,  6:  1447 
    Search in Google Scholar
  • 1c Jairaj V. Koul VK. PharmaChem  2006,  5:  24 
    Search in Google Scholar
  • 1d Turnbull MD. Carter NB. Dennison S. Deacon J. Holley R. Chimia  2004,  58:  159 
    Search in Google Scholar
  • 1e Lang RW. In Chemistry of Organic Fluorine Compounds II   Vol. 187:  ACS Monograph, American Chemical Society; Washington DC: 1995.  p.1143 
    Search in Google Scholar
  • 2 Messina PA. Mange KC. Middleton WJ. J. Fluorine Chem.  1989,  42:  137 
    CrossrefSearch in Google Scholar
  • 3a Goto S. Velder J. Sheikh SE. Sakamoto Y. Mitani M. Elmas S. Adler A. Becker A. Neudörfl J.-M. Lex J. Schmalz H.-G. Synlett  2008,  1361 
  • 3b Murphy ER. Martinelli JR. Zaborenko N. Buchwald SL. Jensen KF. Angew. Chem. Int. Ed.  2007,  46:  1734 
    Search in Google Scholar
  • 3c Sahoo HR. Kralj JG. Jensen KF. Angew. Chem. Int. Ed.  2007,  46:  5704 
    Search in Google Scholar
  • 3d Ushiogi Y. Hase H. Iinuma Y. Takata A. Yoshida J. Chem. Commun.  2007,  2947 
  • 3e Baxendale IR. Ley SV. In New Avenues to Efficient Chemical Synthesis   Seeberger PH. Blume T. Springer; Berlin: 2007.  p.151 
  • 3f Baxendale IR. Hayward JJ. Ley SV. Comb. Chem. High Throughput Screening  2007,  35:  802 
    Search in Google Scholar
  • 3g Hornung CH. Mackley MR. Baxendale IR. Ley SV. Org. Process Res. Dev.  2007,  11:  399 
    Search in Google Scholar
  • 3h Chemical Micro Process Engineering: Processing and Plants   Hessel V. Löwe H. Müller A. Kolb G. Wiley-VCH; Weinheim: 2005. 
  • 3i Hessel V. Löwe H. Schönfeld F. Chem. Eng. Sci.  2005,  60:  2479 
    Search in Google Scholar
  • 3j Meschke F. Riebler G. Hessel V. Schürer J. Baier T. Chem. Eng. Technol.  2005,  28:  465 
    Search in Google Scholar
  • 3k Hodge P. Ind. Eng. Chem. Res.  2005,  44:  8542 
    Search in Google Scholar
  • 3l Luckarift HR. Nadeau LJ. Spain JC. Chem. Commun.  2005,  383 
  • 3m Lee CKY. Holmes AB. Ley SV. McConvey IF. Al-Duri B. Leeke GA. Santos RCD. Seville JPK. Chem. Commun.  2005,  2175 
  • 3n Jas G. Kirschning A. Chem. Eur. J.  2005,  9:  5708 
    Search in Google Scholar
  • 3o Doku GN. Verboom W. Reinhoudt DN. van den Berg A. Tetrahedron  2005,  61:  2733 
    Search in Google Scholar
  • 3p Kawaguchi T. Miyata H. Ataka K. Mae K. Yoshida J. Angew. Chem. Int. Ed.  2005,  44:  2413 
    Search in Google Scholar
  • 3q Löb P. Löwe P. Hessel V. J. Fluorine Chem.  2004,  125:  1677 
    Search in Google Scholar
  • 3r Kolb G. Hessel V. Chem. Eng. J.  2004,  98:  1 
    Search in Google Scholar
  • 3s Yeong KK. Gavriilidis A. Zapf R. Hessel V. Chem. Eng. Sci.  2004,  59:  3491 
    Search in Google Scholar
  • 3t Yen BKH. Stott NE. Jansen KF. Bawendi MG. Adv. Mater  2003,  15:  1858 
    Search in Google Scholar
  • 3u Ueno K. Kitagawa F. Kitamura N. Lab Chip  2002,  2:  231 
    Search in Google Scholar
  • 3v Hafez AM. Taggi AE. Lectka T. Chem. Eur. J.  2002,  8:  4114 
    Search in Google Scholar
  • 3w Haswell SJ. Skelton V. Trends Anal. Chem.  2000,  19:  389 
    Search in Google Scholar
  • 3x Microreactors: New Technology for Modern Chemistry   Ehrfield W. Hessel V. Löwe H. Wiley-VCH; Weinheim: 2000. 
  • 3y Hafez AM. Taggi AE. Wack H. Drury WJ. Lectka T. Org. Lett.  2000,  2:  3963 
    Search in Google Scholar
  • 3z DeWitt SH. Curr. Opin. Chem. Biol.  1999,  3:  350 
    Search in Google Scholar
  • 4a Gustafsson T. Gilmour R. Seeberger PH. Chem. Commun.  2008,  3022 
  • 4b Singh RP. Meshri DT. Shreeve JM. Adv. Org. Synth.  2006,  2:  291 
    Search in Google Scholar
  • 4c Hudlicky M. In Organic Reactions   Vol. 35:  John Wiley and Sons; New York: 1988.  p.513 
    Search in Google Scholar
  • 5 Baxendale IR. Hayward JJ. Lanners S. Ley SV. Smith CD. Heterogeneous Reactions, In Microreactors in Organic Chemistry and Catalysis   Wirth T. Wiley-VCH; Weinheim: 2008.  Chap. 4.2. p.84-122  
  • 6a Baxendale IR. Deeley J. Griffiths-Jones CM. Ley SV. Saaby S. Tranmer GK. Chem. Commun.  2006,  24:  2566 
    Search in Google Scholar
  • 6b Baxendale IR. Griffiths-Jones CM. Ley SV. Tranmer GK. Synlett  2006,  427 
  • 7a Baxendale IR. Ley SV. Smith C. Tamborini L. Vocia A.-F. J. Comb. Chem.  2008,  in press 
  • 7b Baumann M. Baxendale IR. Ley SV. Smith CD. Tranmer GK. Org. Lett.  2006,  8:  5231 
    Search in Google Scholar
  • 8a Baumann M. Baxendale IR. Ley SV. Nikbin N. Smith CD. Org. Biomol. Chem.  2008,  6:  1587 
    Search in Google Scholar
  • 8b Baumann M. Baxendale IR. Ley SV. Nikbin N. Smith CD. Tierney JP. Org. Biomol. Chem.  2008,  6:  1577 
    Search in Google Scholar
  • 8c Smith CJ. Iglesias-Sigüenza FJ. Baxendale IR. Ley SV. Org. Biomol. Chem.  2007,  5:  2758 
    Search in Google Scholar
  • 9a Smith CD. Baxendale IR. Tranmer GK. Baumann M. Smith SC. Lewthwaite RA. Ley SV. Org. Biomol. Chem.  2007,  5:  1562 
    Search in Google Scholar
  • 9b Smith CD. Baxendale IR. Lanners S. Hayward JJ. Smith SC. Ley SV. Org. Biomol. Chem.  2007,  5:  1559 
    Search in Google Scholar
  • 9c Baxendale IR. Ley SV. Smith CD. Tranmer GK. Chem. Commun.  2006,  46:  4835 
    Search in Google Scholar
  • 10 Smith CD. Baxendale IR. Tranmer GK. Baumann M. Smith SC. Lewthwaite RA. Ley SV. Org. Biomol. Chem.  2007,  5:  1562 
    CrossrefSearch in Google Scholar
  • 14 Lal GS. Pez GP. Pesaresi RJ. Prozonic FM. Cheng H. J. Org. Chem.  1999,  64:  7048 
    CrossrefSearch in Google Scholar
  • 16 Tse MK. Bhor S. Klawonn M. Anilkumar G. Jiao H. Döbler C. Spannenberg A. Mägelein W. Hugl H. Beller M. Chem. Eur. J.  2006,  12:  1855 
    CrossrefSearch in Google Scholar
  • 17 Phillips AJ. Uto Y. Wipf P. Reno MJ. Williams DR. Org. Lett.  2000,  2:  1165 
    CrossrefPubMedSearch in Google Scholar
11

Vapourtec R2+/R4 units are available from Vapourtec Ltd, Place Farm, Ingham, Suffolk, IP31 1NQ, UK. Website: http://www.vapourtec.co.uk. See also http://leyitc.ch.cam.ac.uk/equipment.html for images of the equipment.

12

Commercially available Omnifit® glass chromatography columns with adjustable height-end pieces(plunger). Typically, the polymer-supported reagent is placed in an appropriately sized Omnifit® column, usually 10 mm bore by 150 mm length, or shorter and the plungers are adjusted to relevant bed heights and the polymer swelled/washed with solvent. Website: http://www.omnifit.com.

13

Available from Macherey-Nagel GmbH & Co. Dueren, Germany.

15

Oxazoline synthesis in the total synthesis of (-)-hennoxazole A: Ley, S. V. unpublished results.