Synthesis, Inhaltsverzeichnis PAPER© Georg Thieme Verlag Stuttgart · New YorkN-Arylation of 1,4,7,10-TetraazacyclododecanesMichael Subat, Burkhard König*Institut für Organische Chemie, Universität Regensburg, 93040 Regensburg, GermanyFax: +49(941)5431717; e-Mail: burkhard.koenig@chemie.uniregensburg.de; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract Palladium-catalyzed N-arylation reactions provide acces to N-aryl-substituted and N-aryl-bridged 1,4,7,10-tetraazacyclododecanes. Yields of arylation products are low with simple haloarenes, whereas reactions with pyridine derivatives give substituted cyclens in moderate to satisfactory yields. Keywords azamacrocycle - palladium - N-arylation Volltext Referenzen References <A NAME="RZ05201SS-1">1</A> Kaden T. Weller H. Neuburger M. Zehnder M. Helv. Chim. Acta 1997, 80: 2315 <A NAME="RZ05201SS-2">2</A> Zhang XX. Izatt RM. Bradshaw JS. Krakowiak KE. Coord. Chem. Rev. 1998, 174: 179 <A NAME="RZ05201SS-3">3</A> Chantson TE. Hancock RD. Inorg. Chim. Acta 1995, 230: 165 <A NAME="RZ05201SS-4">4</A> Fabbrizzi L. Licchelli M. Pallavicini P. Perotti A. Taglietti A. Sacchi D. Chem.-Eur.J. 1996, 2: 75 <A NAME="RZ05201SS-5">5</A> Gaspar M. Grazina R. Bodor A. Farkas E. Santos MA. J. Chem. Soc., Dalton Trans. 1999, 799 <A NAME="RZ05201SS-6">6</A> Lecomte C. Dahaoui-Gindrey V. Chollet H. Gros C. Mishra AK. Barbette F. Pullumbi P. Guilard R. Inorg. Chem. 1997, 36: 3827 <A NAME="RZ05201SS-7">7</A> Luckay RC. Hancock RD. J. Chem. Soc., Dalton Trans. 1991, 1491 <A NAME="RZ05201SS-8">8</A> Kimura E. Kikuta E. Prog. React. Kinet. 2000, 25: 1 <A NAME="RZ05201SS-9">9</A> Fujioka H. Koike T. Yamada N. Kimura E. Heterocycles 1996, 42: 775 <A NAME="RZ05201SS-10">10</A> Koike T. Takashige M. Kimura E. Fujioka H. Shiro M. Chem.-Eur. J. 1996, 2: 617 <A NAME="RZ05201SS-11">11</A> Aoki S. Kimura E. J. Am. Chem. Soc. 2000, 122: 4542 <A NAME="RZ05201SS-12">12</A> Kimura E. Koike T. Chem. Commun. 1998, 1495 <A NAME="RZ05201SS-13">13</A> König B. Pelka M. Klein M. Dix I. Jones PG. Lex J. J. Inclusion Phenom. 2000. 37: p.39 , and cited references <A NAME="RZ05201SS-14">14</A> Denat F. Brandes S. Guilard R. Synlett 2000, 561 <A NAME="RZ05201SS-15">15</A> Filali A. Yaouanc J.-J. Handel H. Angew. Chem. Int. Ed. Engl. 1991, 30: 560 <A NAME="RZ05201SS-16">16</A> Hartwig JF. Acc. Chem. Res. 1998, 31: 852 <A NAME="RZ05201SS-17">17</A> Singer RA. Sadighi JP. Buchwald SL. J. Am. Chem. Soc. 1998, 120: 213 <A NAME="RZ05201SS-18">18</A> Brandes S. Gros C. Denat F. Pullumbi P. Guilard R. Bull. Soc. Chim. Fr. 1996, 133: 65 <A NAME="RZ05201SS-19">19</A> Koike T. Gotoh T. Aoki S. Kimura E. Shiro M. Inorg. Chim. Acta 1998, 270: 424 <A NAME="RZ05201SS-20">20</A> Wolfe JP. Buchwald SL. J. Org. Chem. 2000, 65: 1144 <A NAME="RZ05201SS-21">21</A> Wolfe JP. Sadighi HT. Yin J. Buchwald SL. J. Org. Chem. 2000, 65: 1158 <A NAME="RZ05201SS-22">22</A> Wolfe JP. Marcoux J.-F. Buchwald SL. Acc. Chem. Res. 1998, 31: 805 <A NAME="RZ05201SS-23">23</A> Old DW. Harris MC. Buchwald SL. Org. Lett. 2000, 2: 1403 <A NAME="RZ05201SS-24">24</A> Mann G. Hartwig JF. Driver MS. Fernández-Rivas C. J. Am. Chem. Soc. 1998, 120: 827 <A NAME="RZ05201SS-25">25</A> Lam PYS. Deudon S. Averill KM. Li R. He MY. DeShong P. Clark CG. J. Am. Chem. Soc. 2000, 122: 7600 <A NAME="RZ05201SS-26">26</A> Zhang X.-X. Buchwald SL. J. Org. Chem. 2000, 65: 8027 <A NAME="RZ05201SS-27">27</A> Witulski B. Synlett 1999, 1223 <A NAME="RZ05201SS-28">28</A> Wolfe JP. Buchwald SL. J. Org. Chem. 1997, 62: 6066 <A NAME="RZ05201SS-29">29</A> The calculation was performed with the modelling software SPARTAN using the MMFF force field and a conformer search algorithm. <A NAME="RZ05201SS-30">30</A> Wolfe JP. Buchwald SL. Angew. Chem. Int. Ed. 1999, 38: 2413 <A NAME="RZ05201SS-31">31</A> Zhang X.-X. Buchwald SL. J. Org. Chem. 2000, 65: 8027 <A NAME="RZ05201SS-32">32</A> Tamaru Y. Yamada Y. Yoshida Z. Synthesis 1983, 474 <A NAME="RZ05201SS-33">33</A> Hatanaka Y. Goda K. Okahara Y. Tetrahedron 1994, 50: 8301 <A NAME="RZ05201SS-34">34</A> Hirano T. Kikuchi K. Urano Y. Higuchi T. Nagano T. Angew. Chem. Int. Ed. 2000, 39: 1052 <A NAME="RZ05201SS-35">35</A> Prasad JS. Okuniewicz FJ. Delaney EJ. Dischino DD. J. Chem. Soc., Perkin Trans. 1 1991, 3329 <A NAME="RZ05201SS-36">36</A> Dumont A. Jacques V. Qixiu P. Desreux JF. Tetrahedron Lett. 1994, 35: 3707