Synthesis, Table of Contents PAPER© Georg Thieme Verlag Stuttgart ˙ New YorkPalladium-Catalysed Direct Arylation of SydnonesArantxa Rodriguez, Wesley J. Moran*Department of Chemical & Biological Sciences, University of Huddersfield, Queensgate, Huddersfield, HD1 3DH, UKFax: +44(1484)472182; e-Mail: w.j.moran@hud.ac.uk; Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract Conditions for the palladium-catalysed direct arylation of sydnones with aryl iodides and bromides are revealed. Key words palladium - cross-coupling - heterocycles - catalysis - arylations Full Text References References For reviews on sydnones, see: <A NAME="RP10908SS-1A">1a</A> Stewart FHC. Chem. Rev. 1964, 64: 129 <A NAME="RP10908SS-1B">1b</A> Newton CG. Ramsden CA. Tetrahedron 1982, 38: 1965 <A NAME="RP10908SS-1C">1c</A> Ollis WD. Ramsden CA. Adv. Heterocycl. Chem. 1976, 19: 1 <A NAME="RP10908SS-2A">2a</A> Wagner HA. Hill JB. J. Med. Chem. 1974, 17: 1337 <A NAME="RP10908SS-2B">2b</A> Hill JB. Ray RE. Wagner H. Aspinall RL. J. Med. Chem. 1975, 18: 50 <A NAME="RP10908SS-2C">2c</A> Dunkley CS. Thomas CJ. Bioorg. Med. Chem. Lett. 2003, 13: 2899 <A NAME="RP10908SS-2D">2d</A> Moustafa MA. Gineinah MM. Nasr MN. Bayoumi WAH. Arch. Pharm. (Weinheim) 2004, 337: 164 <A NAME="RP10908SS-3A">3a</A> Geoffroy I. Carre B. Lemordant D. Herreyre S. Biensan Ph. ITE Lett. Batter., New Technol. Med. 2000, 1: 20 <A NAME="RP10908SS-3B">3b</A> Chan W. Zhang W. Szeto Y. Mater. Lett. 2000, 42: 280 <A NAME="RP10908SS-3C">3c</A> Tien H. Hwang Y. Wen T. J. Chin. Chem. Soc. 1998, 45: 209 <A NAME="RP10908SS-4">4</A> Sasaki Y. Hirobomi O. Handa M. Nippon Kagaku Kaishi 1993, 11: 1217 ; Chem. Abstr. 1994, 120, 34459t <A NAME="RP10908SS-5A">5a</A> Huisgen R. Grashey R. Angew. Chem. 1962, 74: 29 <A NAME="RP10908SS-5B">5b</A> Vasil’eva VF. Yashunskii VG. Shchukina MN. Zh. Obshch. Khim. 1960, 30: 698 <A NAME="RP10908SS-6">6</A> For a recent example of this reactivity, see: Browne DL. Helm MD. Plant A. Harrity JPA. Angew. Chem. Int. Ed. 2007, 46: 8656 <A NAME="RP10908SS-7">7</A> For the transformation of sydnones into oxadiazolinones with bromine in acetic anhydride, see: Mallur SG. Badami BV. Farmaco 2000, 55: 65 <A NAME="RP10908SS-8A">8a</A> Greco CV. Pesce M. Franco JM. J. Heterocycl. Chem. 1966, 3: 391 <A NAME="RP10908SS-8B">8b</A> Kato H. Ohta M. Bull. Chem. Soc. Jpn. 1959, 32: 282 <A NAME="RP10908SS-9">9</A> Kalinin VN. Min SF. J. Organomet. Chem. 1988, 352: C34 For representative examples, see: <A NAME="RP10908SS-10A">10a</A> Pivsa-Art S. Satoh T. Kawamura Y. Miura M. Nomura M. Bull. Chem. Soc. Jpn. 1998, 71: 467 <A NAME="RP10908SS-10B">10b</A> Bellina F. Calandri C. Cauteruccio S. Rossi R. Tetrahedron 2007, 63: 1970 <A NAME="RP10908SS-10C">10c</A> Flegeau EF. Popkin ME. Greaney MF. Org. Lett. 2008, 10: 2717 <A NAME="RP10908SS-10D">10d</A> For reviews, see: Martin T. Verrier C. Hoarau C. Marsais F. Org. Lett. 2008, 10: 2909 <A NAME="RP10908SS-10E">10e</A> Campeau L.-C. Fagnou K. Chem. Commun. 2006, 1253 <A NAME="RP10908SS-10F">10f</A> Seregin IV. Gevorgyan V. Chem. Soc. Rev. 2007, 36: 1173 <A NAME="RP10908SS-10G">10g</A> Alberico D. Scott ME. Lautens M. Chem. Rev. 2007, 107: 174 <A NAME="RP10908SS-11">11</A> Greco CV. O’Reilly BP. J. Heterocycl. Chem. 1970, 7: 1433 <A NAME="RP10908SS-12">12</A> This mechanism was reported for the Pd-catalysed direct cross-coupling reactions of adenosines with aryl iodides: Storr TE. Firth AG. Wilson K. Darley K. Baumann CG. Fairlamb IJS. Tetrahedron 2008, 64: 6125 <A NAME="RP10908SS-13">13</A> These results suggest that this is a ‘Type 1’ cycloaddition: Sustmann R. Pure Appl. Chem. 1974, 40: 569