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

Constantin Mamat; Anke Flemming; Martin Köckerling; Jörg Steinbach; Frank R. Wuest

doi:10.1055/s-0029-1216947

PAPER

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

Constantin Mamat*^a, Anke Flemming^b, Martin Köckerling^b, Jörg Steinbach^a, Frank R. Wuest^c
^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

Abstract

All articles of this category

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.

Key words

Staudinger ligation - traceless - click chemistry - P-C cross-coupling - palladium-catalyzed

Full Text

References

<A NAME="RT05009SS-1A">1a</A> Köhn M. Breinbauer R. Angew. Chem. Int. Ed. 2004, 43: 3106 ; Angew. Chem. 2004, 116, 3168

<A NAME="RT05009SS-1B">1b</A> Gololobov YG. Kasukhin LF. Tetrahedron 1992, 48: 1353

<A NAME="RT05009SS-2A">2a</A> Lin FL. Hoyt HM. van Halbeek H. Bergman RG. Bertozzi CR. J. Am. Chem. Soc. 2005, 127: 2686

<A NAME="RT05009SS-2B">2b</A> Soellner MB. Nilsson BL. Raines RT. J. Am. Chem. Soc. 2006, 128: 8820

<A NAME="RT05009SS-3A">3a</A> Bianchi A. Russo A. Bernardi A. Tetrahedron: Asymmetry 2005, 16: 381

<A NAME="RT05009SS-3B">3b</A> Bianchi A. Bernardi A. J. Org. Chem. 2006, 71: 4565

<A NAME="RT05009SS-3C">3c</A> Saxon E. Luchansky SJ. Hang HC. Yu C. Lee SC. Bertozzi CR. J. Am. Chem. Soc. 2002, 124: 14893

<A NAME="RT05009SS-4">4</A> Grandjean C. Boutonnier A. Guerreiro C. Fournier J.-M. Mulard LA. J. Org. Chem. 2005, 70: 7123

<A NAME="RT05009SS-5A">5a</A> Kleineweischede R. Hackenberger CPR. Angew. Chem. Int. Ed. 2008, 47: 5984 ; Angew. Chem. 2008, 120, 6073

<A NAME="RT05009SS-5B">5b</A> 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

<A NAME="RT05009SS-5C">5c</A> Merkx R. Rijkers DTS. Kemmink J. Liskamp RMJ. Tetrahedron Lett. 2003, 44: 4515

<A NAME="RT05009SS-5D">5d</A> Tam A. Soellner MB. Raines RT. Org. Biomol. Chem. 2008, 1173

<A NAME="RT05009SS-5E">5e</A> Masson G. den Hartog T. Schoemaker HE. Hiemstra H. van Maarseveen JH. Synlett 2006, 865

<A NAME="RT05009SS-6A">6a</A> Wang CC. Seo TS. Li Z. Ruparel H. Ju J. Bioconjugate Chem. 2003, 14: 697

<A NAME="RT05009SS-6B">6b</A> Chang PV. Prescher JA. Hangauer MJ. Bertozzi CR. J. Am. Chem. Soc. 2007, 129: 8400

<A NAME="RT05009SS-6C">6c</A> Hangauer MJ. Bertozzi CR. Angew. Chem. Int. Ed. 2008, 47: 2394 ; Angew. Chem. 2008, 120, 2428

<A NAME="RT05009SS-7">7</A> Nisic F. Bernardi A. Carbohydr. Res. 2008, 343: 1636

<A NAME="RT05009SS-8">8</A> Zhang J. Wang H. Xian M. Org. Lett. 2009, 11: 477

Reviews:

<A NAME="RT05009SS-9A">9a</A> Heck RF. Palladium Reagents in Organic Synthesis Academic Press; London: 1985.

<A NAME="RT05009SS-9B">9b</A> de Meijere A. Meier F. Angew. Chem., Int. Ed. Engl. 1994, 33: 2379 ; Angew. Chem. 1994, 106, 2473

<A NAME="RT05009SS-9C">9c</A> Heck RF. In Comprehensive Organic Synthesis Vol. 4: Trost BM. Fleming I. Semmelhack MF. Pergamon; Oxford: 1991. p.833

<A NAME="RT05009SS-9D">9d</A> Cabri W. Candiani I. Acc. Chem. Res. 1995, 28: 2

<A NAME="RT05009SS-10A">10a</A> Tunney SE. Stille JK. J. Org. Chem. 1987, 52: 748

<A NAME="RT05009SS-10B">10b</A> Beletskaya IP. Veits YA. Lekunkin VA. Voss VL. Izv. Akad. Nauk, Ser. Khim. 1992, 1645 ; Chem. Abstr. 1993, 118, 102064

<A NAME="RT05009SS-11A">11a</A> Herd O. Heßler A. Hingst M. Tepper M. Stelzer O. J. Organomet. Chem. 1996, 522: 69

<A NAME="RT05009SS-11B">11b</A> Herd O. Heßler A. Hingst M. Machnitzki P. Tepper M. Stelzer O. Catal. Today 1998, 42: 413

<A NAME="RT05009SS-12">12</A> Vallette H. Pican S. Boudou C. Levillain J. Plaquevent J.-C. Gaumont A.-C. Tetrahedron Lett. 2006, 47: 5191

<A NAME="RT05009SS-13">13</A> Lipshutz BH. Buzard DJ. Yun CS. Tetrahedron Lett. 1999, 40: 201

<A NAME="RT05009SS-14">14</A> Mäding P. Füchtner F. Wüst F. Appl. Radiat. Isot. 2005, 63: 329

<A NAME="RT05009SS-15">15</A> Neises B. Steglich S. Angew. Chem., Int. Ed. Engl. 1978, 17: 522 ; Angew. Chem. 1978, 90, 556

<A NAME="RT05009SS-16">16</A> Pautard-Cooper A. Evans SA. J. Org. Chem. 1989, 54: 2485

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.

<A NAME="RT05009SS-18">18</A> CRC Handbook of Chemistry and Physics Weast RC. Astle MJ. CRC Press Inc.; Boca Raton: 1980. p.F-215

<A NAME="RT05009SS-19A">19a</A> Schmidbaur H. J. Organomet. Chem. 1980, 200: 287

<A NAME="RT05009SS-19B">19b</A> Brunel JM. Faure B. Maffei M. Coord. Chem. Rev. 1998, 178-180: 665

<A NAME="RT05009SS-20A">20a</A> Oshiki T. Imamoto T. J. Am. Chem. Soc. 1992, 114: 3975

<A NAME="RT05009SS-20B">20b</A> Imamoto T. Oshiki T. Onozawa T. Matsuo M. Hikosaka T. Yanagawa M. Heteroat. Chem. 1992, 3: 563

<A NAME="RT05009SS-20C">20c</A> Moulin D. Bago S. Bauduin C. Darcel C. Jugé S. Tetrahedron: Asymmetry 2000, 11: 3939

<A NAME="RT05009SS-21">21</A> Pellon P. Le Goaster C. Marchand G. Martin B. Toupet L. Heteroat. Chem. 1997, 8: 123

<A NAME="RT05009SS-22A">22a</A> Imamoto T. Oshiki T. Onozawa T. Kusumoto T. Sato K. J. Am. Chem. Soc. 1990, 112: 5244

<A NAME="RT05009SS-22B">22b</A> McNulty J. Zhou Y. Tetrahedron Lett. 2004, 45: 407

<A NAME="RT05009SS-23">23</A> Review: Carboni B. Monnier L. Tetrahedron 1999, 55: 1197

<A NAME="RT05009SS-24">24</A> Dornhaus F. Bolte M. Lerner H.-W. Wagner M. Eur. J. Inorg. Chem. 2006, 1777

<A NAME="RT05009SS-25">25</A> Corbridge DEC. Phosphorus, an Outline of its Chemistry, Biochemistry and Technology 4th ed.: Elsevier; Amsterdam: 1990. p.680-681

<A NAME="RT05009SS-26">26</A> Joosten JAF. Evers B. van Summeren RP. Kamerling JP. Vliegenthart JFG. Eur. J. Org. Chem. 2003, 3569

<A NAME="RT05009SS-27">27</A> Sheldrick GM. SHELXS-97 and SHELXL-97, Programs for the Solution and Refinement of Crystal Structures University of Göttingen; Göttingen: 1997.

<A NAME="RT05009SS-28">28</A> 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

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

<A NAME="RT05009SS-30">30</A> Spratt MP. Dorn HC. Anal. Chem. 1984, 56: 2038

<A NAME="RT05009SS-31">31</A> Theocharis AB. Alexandrou NE. Terzis A. J. Heterocycl. Chem. 1990, 27: 1741

<A NAME="RT05009SS-32">32</A> Nilsson BL. Kiessling LL. Raines RT. Org. Lett. 2000, 2: 1939