Synthesis 2009(19): 3311-3321  
DOI: 10.1055/s-0029-1216947
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Benzoate-Functionalized Phosphanes as Novel Building Blocks for the Traceless Staudinger Ligation

Constantin Mamat*a, Anke Flemmingb, Martin Köckerlingb, Jörg Steinbacha, Frank R. Wuestc
a Institut für Radiopharmazie, Forschungszentrum Dresden-Rossendorf e. V., Postfach: 50 01 19, 01314 Dresden, Germany
Fax: +49(351)2602915; e-Mail: c.mamat@fzd.de;
b Institut für Chemie, Universität Rostock, Albert-Einstein-Straße 3a, 18059 Rostock, Germany
c Department of Oncologic Imaging, Cross Cancer Institute, University of Alberta, Edmonton, AB, T6G 1Z2, Canada
Weitere Informationen

Publikationsverlauf

Received 2 March 2009
Publikationsdatum:
21. August 2009 (online)

Abstract

A new synthetic pathway for the preparation of benzoate-functionalized phosphanes for microwave-mediated traceless Staudinger ligations is described. Novel phosphane derivatives based on 4-substituted iodophenyl benzoates were prepared via palladium(II)-catalyzed P-C cross-coupling reaction strategy in high yields. The application of microwave conditions for the ligation reactions reduced the reaction time considerably. An approach to fast and facile labeling strategies using this ligation was established.

    References

  • 1a Köhn M. Breinbauer R. Angew. Chem. Int. Ed.  2004,  43:  3106 ; Angew. Chem. 2004, 116, 3168
  • 1b Gololobov YG. Kasukhin LF. Tetrahedron  1992,  48:  1353 
  • 2a Lin FL. Hoyt HM. van Halbeek H. Bergman RG. Bertozzi CR. J. Am. Chem. Soc.  2005,  127:  2686 
  • 2b Soellner MB. Nilsson BL. Raines RT. J. Am. Chem. Soc.  2006,  128:  8820 
  • 3a Bianchi A. Russo A. Bernardi A. Tetrahedron: Asymmetry  2005,  16:  381 
  • 3b Bianchi A. Bernardi A. J. Org. Chem.  2006,  71:  4565 
  • 3c Saxon E. Luchansky SJ. Hang HC. Yu C. Lee SC. Bertozzi CR. J. Am. Chem. Soc.  2002,  124:  14893 
  • 4 Grandjean C. Boutonnier A. Guerreiro C. Fournier J.-M. Mulard LA. J. Org. Chem.  2005,  70:  7123 
  • 5a Kleineweischede R. Hackenberger CPR. Angew. Chem. Int. Ed.  2008,  47:  5984 ; Angew. Chem. 2008, 120, 6073
  • 5b David O. Meester WJN. Bieräugel H. Schoemaker HE. Hiemstra H. van Maarseveen JH. Angew. Chem. Int. Ed.  2003,  42:  4373 ; Angew. Chem. 2003, 115, 4509
  • 5c Merkx R. Rijkers DTS. Kemmink J. Liskamp RMJ. Tetrahedron Lett.  2003,  44:  4515 
  • 5d Tam A. Soellner MB. Raines RT.  Org. Biomol. Chem.  2008,  1173 
  • 5e Masson G. den Hartog T. Schoemaker HE. Hiemstra H. van Maarseveen JH. Synlett  2006,  865 
  • 6a Wang CC. Seo TS. Li Z. Ruparel H. Ju J. Bioconjugate Chem.  2003,  14:  697 
  • 6b Chang PV. Prescher JA. Hangauer MJ. Bertozzi CR. J. Am. Chem. Soc.  2007,  129:  8400 
  • 6c Hangauer MJ. Bertozzi CR. Angew. Chem. Int. Ed.  2008,  47:  2394 ; Angew. Chem. 2008, 120, 2428
  • 7 Nisic F. Bernardi A. Carbohydr. Res.  2008,  343:  1636 
  • 8 Zhang J. Wang H. Xian M. Org. Lett.  2009,  11:  477 
  • Reviews:
  • 9a Heck RF. Palladium Reagents in Organic Synthesis   Academic Press; London: 1985. 
  • 9b de Meijere A. Meier F. Angew. Chem., Int. Ed. Engl.  1994,  33:  2379 ; Angew. Chem. 1994, 106, 2473
  • 9c Heck RF. In Comprehensive Organic Synthesis   Vol. 4:  Trost BM. Fleming I. Semmelhack MF. Pergamon; Oxford: 1991.  p.833 
  • 9d Cabri W. Candiani I. Acc. Chem. Res.  1995,  28:  2 
  • 10a Tunney SE. Stille JK. J. Org. Chem.  1987,  52:  748 
  • 10b Beletskaya IP. Veits YA. Lekunkin VA. Voss VL. Izv. Akad. Nauk, Ser. Khim.  1992,  1645 ; Chem. Abstr. 1993, 118, 102064
  • 11a Herd O. Heßler A. Hingst M. Tepper M. Stelzer O. J. Organomet. Chem.  1996,  522:  69 
  • 11b Herd O. Heßler A. Hingst M. Machnitzki P. Tepper M. Stelzer O. Catal. Today  1998,  42:  413 
  • 12 Vallette H. Pican S. Boudou C. Levillain J. Plaquevent J.-C. Gaumont A.-C. Tetrahedron Lett.  2006,  47:  5191 
  • 13 Lipshutz BH. Buzard DJ. Yun CS. Tetrahedron Lett.  1999,  40:  201 
  • 14 Mäding P. Füchtner F. Wüst F. Appl. Radiat. Isot.  2005,  63:  329 
  • 15 Neises B. Steglich S. Angew. Chem., Int. Ed. Engl.  1978,  17:  522 ; Angew. Chem. 1978, 90, 556
  • 16 Pautard-Cooper A. Evans SA. J. Org. Chem.  1989,  54:  2485 
  • 18 CRC Handbook of Chemistry and Physics   Weast RC. Astle MJ. CRC Press Inc.; Boca Raton: 1980.  p.F-215 
  • 19a Schmidbaur H. J. Organomet. Chem.  1980,  200:  287 
  • 19b Brunel JM. Faure B. Maffei M. Coord. Chem. Rev.  1998,  178-180:  665 
  • 20a Oshiki T. Imamoto T. J. Am. Chem. Soc.  1992,  114:  3975 
  • 20b Imamoto T. Oshiki T. Onozawa T. Matsuo M. Hikosaka T. Yanagawa M. Heteroat. Chem.  1992,  3:  563 
  • 20c Moulin D. Bago S. Bauduin C. Darcel C. Jugé S. Tetrahedron: Asymmetry  2000,  11:  3939 
  • 21 Pellon P. Le Goaster C. Marchand G. Martin B. Toupet L. Heteroat. Chem.  1997,  8:  123 
  • 22a Imamoto T. Oshiki T. Onozawa T. Kusumoto T. Sato K. J. Am. Chem. Soc.  1990,  112:  5244 
  • 22b McNulty J. Zhou Y. Tetrahedron Lett.  2004,  45:  407 
  • 23 Review: Carboni B. Monnier L. Tetrahedron  1999,  55:  1197 
  • 24 Dornhaus F. Bolte M. Lerner H.-W. Wagner M. Eur. J. Inorg. Chem.  2006,  1777 
  • 25 Corbridge DEC. Phosphorus, an Outline of its Chemistry, Biochemistry and Technology   4th ed.:  Elsevier; Amsterdam: 1990.  p.680-681  
  • 26 Joosten JAF. Evers B. van Summeren RP. Kamerling JP. Vliegenthart JFG. Eur. J. Org. Chem.  2003,  3569 
  • 27 Sheldrick GM. SHELXS-97 and SHELXL-97, Programs for the Solution and Refinement of Crystal Structures   University of Göttingen; Göttingen: 1997. 
  • 28 Lacoudre N. Le Borgne A. Spassky N. Vairon J.-P. Le Barny P. Dubois J.-C. Esselin S. Friedrich C. Noël C. Mol. Cryst. Liq. Cryst.  1988,  115:  113 
  • 30 Spratt MP. Dorn HC. Anal. Chem.  1984,  56:  2038 
  • 31 Theocharis AB. Alexandrou NE. Terzis A. J. Heterocycl. Chem.  1990,  27:  1741 
  • 32 Nilsson BL. Kiessling LL. Raines RT. Org. Lett.  2000,  2:  1939 
17

CCDC 708661 (compound 4a), and 708662 (compound 10c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

29

Compound 5f was prepared according to the procedure given in reference 28 with 1-bromo-2-fluoroethane instead of 2-bromoethanol.