Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart ˙ New York Palladium-Catalysed Direct Arylation of Sydnones Arantxa 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 All articles of this category 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: 1a Stewart FHC. Chem. Rev. 1964, 64: 129 1b Newton CG. Ramsden CA. Tetrahedron 1982, 38: 1965 1c Ollis WD. Ramsden CA. Adv. Heterocycl. Chem. 1976, 19: 1 2a Wagner HA. Hill JB. J. Med. Chem. 1974, 17: 1337 2b Hill JB. Ray RE. Wagner H. Aspinall RL. J. Med. Chem. 1975, 18: 50 2c Dunkley CS. Thomas CJ. Bioorg. Med. Chem. Lett. 2003, 13: 2899 2d Moustafa MA. Gineinah MM. Nasr MN. Bayoumi WAH. Arch. Pharm. (Weinheim) 2004, 337: 164 3a Geoffroy I. Carre B. Lemordant D. Herreyre S. Biensan Ph. ITE Lett. Batter., New Technol. Med. 2000, 1: 20 3b Chan W. Zhang W. Szeto Y. Mater. Lett. 2000, 42: 280 3c Tien H. Hwang Y. Wen T. J. Chin. Chem. Soc. 1998, 45: 209 4 Sasaki Y. Hirobomi O. Handa M. Nippon Kagaku Kaishi 1993, 11: 1217 ; Chem. Abstr. 1994, 120, 34459t 5a Huisgen R. Grashey R. Angew. Chem. 1962, 74: 29 5b Vasil’eva VF. Yashunskii VG. Shchukina MN. Zh. Obshch. Khim. 1960, 30: 698 6 For a recent example of this reactivity, see: Browne DL. Helm MD. Plant A. Harrity JPA. Angew. Chem. Int. Ed. 2007, 46: 8656 7 For the transformation of sydnones into oxadiazolinones with bromine in acetic anhydride, see: Mallur SG. Badami BV. Farmaco 2000, 55: 65 8a Greco CV. Pesce M. Franco JM. J. Heterocycl. Chem. 1966, 3: 391 8b Kato H. Ohta M. Bull. Chem. Soc. Jpn. 1959, 32: 282 9 Kalinin VN. Min SF. J. Organomet. Chem. 1988, 352: C34 For representative examples, see: 10a Pivsa-Art S. Satoh T. Kawamura Y. Miura M. Nomura M. Bull. Chem. Soc. Jpn. 1998, 71: 467 10b Bellina F. Calandri C. Cauteruccio S. Rossi R. Tetrahedron 2007, 63: 1970 10c Flegeau EF. Popkin ME. Greaney MF. Org. Lett. 2008, 10: 2717 10d For reviews, see: Martin T. Verrier C. Hoarau C. Marsais F. Org. Lett. 2008, 10: 2909 10e Campeau L.-C. Fagnou K. Chem. Commun. 2006, 1253 10f Seregin IV. Gevorgyan V. Chem. Soc. Rev. 2007, 36: 1173 10g Alberico D. Scott ME. Lautens M. Chem. Rev. 2007, 107: 174 11 Greco CV. O’Reilly BP. J. Heterocycl. Chem. 1970, 7: 1433 12 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 13 These results suggest that this is a ‘Type 1’ cycloaddition: Sustmann R. Pure Appl. Chem. 1974, 40: 569