First use of a palladium complex with a thiosemicarbazone ligand as catalyst precursor for the Heck reaction

Tetrahedron Letters

Volumn 45, Issue 14, 2004, Pages 2923-2926

  Kovala Demertzi, Dimitra ^a   Yadav, Paras N ^a   Demertzis, Mavroudis A ^a   Jasiski, Jerry P ^b   Andreadaki, Fotini J ^c   Kostas, Ioannis D ^c  

^a UNIVERSITY OF IOANNINA   (Greece)

^b KEENE STATE COLLEGE   (United States)

^c INSTITUTE OF BIOLOGY   (Greece)

Author keywords

Heck reaction; Homogeneous catalysis; O, N, S ligand; Palladium complex; Phosphine free ligand; Thiosemicarbazone

Indexed keywords

ARGON; BROMINE DERIVATIVE; LIGAND; ORGANIC COMPOUND; PALLADIUM COMPLEX; PHOSPHORUS; SALICYLALDEHYDE; STYRENE; THIOSEMICARBAZONE; THIOSEMICARBAZONE DERIVATIVE;

ARTICLE; ARYLATION; BROMINATION; CATALYSIS; CATALYST; CRYSTAL STRUCTURE; ELECTRON TRANSPORT; HECK REACTION; ORGANIC CHEMISTRY; PRECURSOR; QUANTUM YIELD; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 1642350799     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.062     Document Type: Article

References (61)

1. Recent leading monographs and reviews: Tsuji J. Palladium Reagents and Catalysts. 1995;John Wiley & Sons, Chichester.
2. Reetz M.T. Davies S.G., Murahashi S.-I. Transition Metal Catalysed Reactions. 1999;Blackwell Science, Oxford.
3. Beletskaya I.P., Cheprakov A.V. Chem. Rev. 100:2000;3009-3066.
4. Whitecombe N.J., Hii K.K.(Mimi), Gibson S.E. Tetrahedron. 57:2001;7449-7476.
5. Littke A.F., Fu G.C. Angew. Chem. Int. Ed. 41:2002;4176-4211.
6. Tucker C.E., de Vries J.G. Top. Catal. 19:2002;111-118.
7. Dounay A.B., Overman L.E. Chem. Rev. 103:2003;2945-2963.
8. Recent selected papers: Stambuli J.P., Stauffer S.R., Shaughnessy K.H., Hartwig J.F. J. Am. Chem. Soc. 123:2001;2677-2678.
9. Feuerstein M., Doucet H., Santelli M. J. Org. Chem. 66:2001;5923-5925.
10. Li G.Y., Zheng G., Noonan A.F. J. Org. Chem. 66:2001;8677-8681.
11. Schnyder A., Indolese A.F., Studer M., Blaser H.-U. Angew. Chem. Int. Ed. 41:2002;3668-3671.
12. Imbos R., Minnaard A.J., Feringa B.L. J. Am. Chem. Soc. 124:2002;184-185.
13. Morales-Morales D., Redón R., Zheng Y., Dilworth J.R. Inorg. Chim. Acta. 328:2002;39-44.
14. Kondolff I., Doucet H., Santelli M. Tetrahedron Lett. 44:2003;8487-8491.
15. Tu T., Hou X.-L., Dai L.-X. Org. Lett. 5:2003;3651-3653.
16. Hierso J.-C., Fihri A., Amardeil R., Meunier P., Doucet H., Santelli M., Donnadieu B. Organometallics. 22:2003;4490-4499.
17. Imbos R., Minnaard A.J., Feringa B.L. J. Chem. Soc., Dalton Trans. 2003;2017-2023.
18. Catsoulacos D.P., Steele B.R., Heropoulos G.A., Micha-Screttas M., Screttas C.G. Tetrahedron Lett. 44:2003;4575-4578.
19. Kostas I.D., Steele B.R., Terzis A., Amosova S.V. Tetrahedron. 59:2003;3467-3473.
20. For air-stable phosphine catalysts, see for example Refs. [2c,f].
21. Recent selected papers: Tulloch A.A.D., Danopoulos A.A., Tooze R.P., Cafferkey S.M., Kleinhenz S., Hursthouse M.B. Chem. Commun. 2000;1247-1248.
22. Albéniz A.C., Espinet P., Martín-Ruiz B., Milstein D. J. Am. Chem. Soc. 123:2001;11504-11505.
23. Peris E., Loch J.A., Mata J., Crabtree R.H. Chem. Commun. 2001;201-202.
24. Selvakumar K., Zapf A., Beller M. Org. Lett. 4:2002;3031-3033.
25. Jung I.G., Son S.U., Park K.H., Chung K.-C., Lee J.W., Chung Y.K. Organometallics. 22:2003;4715-4720.
26. Díez-Barra E., Guerra J., Hornillos V., Merino S., Tejeda J. Organometallics. 22:2003;4610-4612.
27. Consorti C.S., Zanini M.L., Leal S., Ebeling G., Dupont J. Org. Lett. 5:2003;983-986.
28. Nájera C., Gil-Moltó J., Karlström S., Falvello L.R. Org. Lett. 5:2003;1451-1454.
29. Masllorens J., Moreno-Mañas M., Pla-Quintana A., Roglans A. Org. Lett. 5:2003;1559-1561.
30. Park S.B., Alper H. Org. Lett. 5:2003;3209-3212.
31. Mazet C., Gade L.H. Eur. J. Inorg. Chem. 2003;1161-1168.
32. Recent selected papers: Reetz M.T., Westermann E. Angew. Chem. Int. Ed. 39:2000;165-168.
33. Gruber A.S., Pozebon D., Monteiro A.L., Dupont J. Tetrahedron Lett. 42:2001;7345-7348.
34. Yao Q., Kinney E.P., Yang Z. J. Org. Chem. 68:2003;7528-7531.
35. Schmidt A.F., Smirnov V.V. J. Mol. Catal. A: Chem. 203:2003;75-78.
36. de Vries A.H.M., Mulders J.M.C.A., Mommers J.H.M., Henderickx H.J.W., de Vries J.G. Org. Lett. 5:2003;3285-3288.
37. Willans C.E., Mulders J.M.C.A., de Vries J.G., de Vries A.H.M. J. Organomet. Chem. 687:2003;494-497.
38. Recent selected papers: Quiroga A.G., Perez J.M., López-Solera I., Masaguer J.R., Luque A., Román P., Edwards A., Alonso C., Navarro-Ranninger C. J. Med. Chem. 41:1998;1399-1408.
39. Kovala-Demertzi D., Demertzis M.A., Varagi V., Papageorgiou A., Mourelatos D., Mioglou E., Iakovidou Z., Kotsis A. Chemotherapy. 44:1998;421-426.
40. Varadinova T., Kovala-Demertzi D., Rupelieva M., Demertzis M., Genova P. Acta Virologica. 45:2001;87-94.
41. Iakovidou Z., Papageorgiou A., Demertzis M.A., Mioglou E., Mourelatos D., Kotsis A., Yadav P.N., Kovala-Demertzi D. Anticancer Drugs. 12:2001;65-70.
42. Jouad E.M., Thanh X.D., Bouet G., Bonneau S., Khan M.A. Anticancer Res. 22:2002;1713-1716.
43. Pal I., Basuli F., Mak T.C.W., Bhattacharya S. Angew. Chem. Int. Ed. 40:2001;2923-2925.
44. Dutta S., Basuli F., Peng S.-M., Lee G.-H., Bhattacharya S. New J. Chem. 26:2002;1607-1612.
45. Reetz M.T., Waldvogel S.R., Goddard R. Tetrahedron Lett. 38:1997;5967-5970.
46. Kovala-Demertzi D., Kourkoumelis N., Demertzis M.A., Miller J.R., Frampton C.S., Swearingen J.K., West D.X. Eur. J. Inorg. Chem. 2000;727-734.
47. Kovala-Demertzi D., Demertzis M.A., Miller J.R., Papadopoulou C., Dodorou C., Filousis G. J. Inorg. Biochem. 86:2001;555-563.
48. Yadav P.N., Demertzis M.A., Kovala-Demertzi D., Castineiras A., West D.X. Inorg. Chim. Acta. 332:2002;204-209.
49. Kovala-Demertzi D., Demertzis M.A., Filiou E., Pantazaki A.A., Yadav P.N., Miller J.R., Zheng Y.F., Kyriakidis D.A. Biometals. 16:2003;411-418.
50. Kostas I.D., Screttas C.G. J. Organomet. Chem. 585:1999;1-6.
51. Kostas I.D. J. Chem. Res. (S). 1999;630-631.
52. Kostas I.D. J. Organomet. Chem. 626:2001;221-226.
53. Kostas I.D. J. Organomet. Chem. 634:2001;90-98.
54. Kostas I.D. Inorg. Chim. Acta. 355:2003;424-427.
55. 2PdS: C, 31.4; H, 3.7; Cl, 9.5; N, 11. 0; Pd, 27.9; S, 8.4. Found: C, 31.5; H, 3.7; Cl, 9.3; N, 11.2; Pd, 27.8; S, 8.3.
56. Known compound: Mishra P., Chowdhari D., Katrolia S.P., Agrawal R.K. Hind. Antibiot. Bull. 30:1988;37-39. [Chem. Abstr. 1988; 109, 208128].
57. Yin D.-D., Jiang Y.-L., Shan L. Chin. J. Chem. 19:2001;1136-1140. [Chem. Abstr. 2003; 136, 183890].
58. Kovala-Demertzi D., Domopoulou A., Demertzis M.A., Raptopoulou C.P., Terzis A. Polyhedron. 13:1994;1917-1925.
59. w=0.0262.
60. Kovala-Demertzi D., Miller J.R., Kourkoumelis N., Hadjikakou S.K., Demertzis M.A. Polyhedron. 18:1999;1005-1013.
61. 2l.