Synthesis of molecular chains: phenylene thioether and sulfoxide oligomers

Tetrahedron

Volumn 64, Issue 27, 2008, Pages 6281-6288

  Vicente, José ^a   Abad, José A ^a   López Nicolás, Rosa M ^a  

^a Grupo de Ingenieria Bioquimica   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIIODOBENZENE; 4 PHENYLENE SULFOXIDE; BENZENE 1,4 DITHIOL; BENZENE DERIVATIVE; BROMINE; COPPER; DIIODOMESITYLENE; IODINE; PALLADIUM; PHENYLENE SULFIDE; PHENYLENE THIOETHER; SULFIDE; SULFOXIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; DEALKYLATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

EID: 44349190197     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.04.108     Document Type: Article

References (103)

1. Wu P., Malkoch M., Hunt J.N., Vestberg R., Kaltgrad E., Finn M.G., Fokin V.V., Sharpless K.B., and Hawker C.J. Chem. Commun. (2005) 5775
2. Kihara H., and Tamaoki N. Macromol. Rapid Commun. 27 (2006) 829
3. Abd-El-Aziz A.S. Coord. Chem. Rev. 233 (2002) 177
4. Berresheim A.J., Muller M., and Mullen K. Chem. Rev. 99 (1999) 1747
5. Peris E. Coord. Chem. Rev. 248 (2004) 279
6. Lee J.W., Kim J.H., Kim B.K., Kim J.H., Shin W.S., and Jin S.H. Tetrahedron 62 (2006) 9193
7. Crespo L., Sanclimens G., Pons M., Giralt E., Royo M., and Albericio F. Chem. Rev. 105 (2005) 1663
8. Grayson S.M., and Frechet J.M.J. Chem. Rev. 101 (2001) 3819
9. Bosman A.W., Janssen H.M., and Meijer E.W. Chem. Rev. 99 (1999) 1665
10. Fischer M., and Vogtle F. Angew. Chem., Int. Ed. 38 (1999) 885
11. Caminade A.M., Laurent R., Chaudret B., and Majoral J.P. Coord. Chem. Rev. 180 (1998) 793
12. Tang S.Z., Martinez L.J., Sharma A., and Chai M.H. Org. Lett. 8 (2006) 4421
13. Jiang Y., Wang J.Y., Ma Y.G., Cui Y.X., Zhou Q.F., and Pei J. Org. Lett. 8 (2006) 4287
14. Xu T.H., Lu R., Qiu X.P., Liu X.L., Xue P.C., Tan C.H., Bao C.Y., and Zhao Y.Y. Eur. J. Org. Chem. (2006) 4014
15. Mery D., and Astruc D. Coord. Chem. Rev. 250 (2006) 1965
16. Choi J.S., Ko K.S., Park J.S., Kim Y.H., Kim S.W., and Lee M. Int. J. Pharm. 320 (2006) 171
17. Haag R., and Kratz F. Angew. Chem., Int. Ed. 45 (2006) 1198
18. Grabchev I., Chovelon J.M., and Nedelcheva A. J. Photochem. Photobiol. A-Chem. 183 (2006) 9
19. Smith T.M., Hazelton N., Peteanu L.A., and Wildeman J. J. Phys. Chem. B 110 (2006) 7732
20. Nantalaksakul A., Reddy D.R., Bardeen C.J., and Thayumanavan S. Photosynth. Res. 87 (2006) 133
21. Choi M.S., Yamazaki T., Yamazaki I., and Aida T. Angew. Chem., Int. Ed. 43 (2004) 150
22. Zhao C.C., Zhang Y., Wang C.W., Rothberg L., and Ng M.K. Org. Lett. 8 (2006) 1585
23. Cifuentes M.P., Powell C.E., Morrall J.P., McDonagh A.M., Lucas N.T., Humphrey M.G., Samoc M., Houbrechts S., Asselberghs I., Clays K., Persoons A., and Isoshima T. J. Am. Chem. Soc. 128 (2006) 10819
24. Kato T., Mizoshita N., and Kishimoto K. Angew. Chem., Int. Ed. 45 (2006) 38
25. Manunta M., Nichols B.J., Tan P.H., Sagoo P., Harper J., and George A.J.T. J. Immunol. Methods 314 (2006) 134
26. Helms B., and Frechet J.M.J. Adv. Synth. Catal. 348 (2006) 1125
27. Delort E., Nguyen-Trung N.Q., Darbre T., and Reymond J.L. J. Org. Chem. 71 (2006) 4468
28. Reek J.N.H., Arevalo S., van Heerbeek R., Kamer P.C.J., and van Leeuwen P.W.N.M. Adv. Catal. 49 (2006) 71
29. Astruc D., and Chardac F. Chem. Rev. 101 (2001) 2991
30. Oosterom G.E., Reek J.N.H., Kamer P.C.J., and van Leeuwen P. Angew. Chem., Int. Ed. 40 (2001) 1828
31. Pu L. Chem. Rev. 104 (2004) 1687
32. Johnson R.D., Pinchart A., Badr I.H.A., Gingras M., and Bachas L.G. Electroanalysis 14 (2002) 1419
33. Chen S.H., Shi H.Q., Mastrangelo J.C., and Ou J.J. Prog. Polym. Sci. 21 (1996) 1211
34. Zhang Z.S., and Fan E.K. J. Org. Chem. 70 (2005) 8801
35. Hortholary C., and Coudret C. J. Org. Chem. 68 (2003) 2167
36. Valasek M., Pecka J., Jindrich J., Calleja G., Craig P.R., and Michl J. J. Org. Chem. 70 (2005) 405
37. Magro G., Donnadieu B., Caminade A.M., and Majoral J.P. Chem.-Eur. J. 9 (2003) 2151
38. De Nicola A., Goeb S., and Ziessel R. Tetrahedron Lett. 44 (2004) 7963
39. Dong T.-Y., Lin M.-C., Chiang M.Y.-N., and Wu J.-Y. Organometallics 23 (2004) 3921
40. Hurst S.K., Cifuentes M.P., and Humphrey M.G. Organometallics 21 (2002) 2353
41. Newkome G.R., He E., and Moorefield C.N. Chem. Rev. 99 (1999) 1689
42. Rodríguez J.G., Tejedor J.L., Esquivias J., and Diaz C. Tetrahedron Lett. 44 (2003) 6375
43. Rozalska I., Kulyk P., and KulszewiczBajer I. New J. Chem. 28 (2004) 1235
44. van Heerbeek R., Kamer P.C.J., van Leeuwen P.W.N.M., and Reek J.N.H. Chem. Rev. 102 (2002) 3717
45. Yamamoto K., Higuchi M., Shiki S., Tsuruta M., and Chiba H. Nature 415 (2002) 509
46. Franz N., Kreutzer G., and Klok H.-A. Synlett (2006) 1793
47. Jones T.V., Blatchly R.A., and Tew G.N. Org. Lett. 5 (2003) 3297
48. Vicente J., Abad J.A., and Lopez-Nicolas R.M. Tetrahedron Lett. 46 (2005) 5839
49. Dahan A., Weissberg A., and Portnoy M. Chem. Commun. (2003) 1206
50. In I., and Kim S.Y. J. Polym. Sci., Part A: Polym. Chem. 44 (2006) 2440
51. Geibel J.F., and Campbell R.W. In: Eastmond G.C., Ledwith A., Russo S., and Sigwalt P. (Eds). Comprehensive Polymer Science Vol. 5 (1989), Pergamon, Oxford, UK Chapter 32
52. Wang Y.F., and Hay A.S. Macromolecules 30 (1997) 182
53. Szigeti Z., Malon A., Vigassy T., Csokai V., Grun A., Wygladacz K., Ye N., Xu C., Chebny V.J., Bitter I., Rathore R., Bakker E., and Pretsch E. Anal. Chim. Acta 572 (2006) 1
54. Hartwig J.F. Acc. Chem. Res. 31 (1998) 852
55. Wong Y.-C., Jayanth T.T., and Cheng C.-H. Org. Lett. 8 (2006) 5613
56. Cristau H.J., Chabaud B., and Christol H. Synthesis 11 (1981) 892
57. Takagi K. Chem. Lett. (1987) 2221
58. Fernández-Rodríguez M.A., Shen Q., and Hartwig J.F. J. Am. Chem. Soc. 128 (2006) 2180
59. Barbieri R.S., Bellato C.R., Dias A.K.C., and Massabni A.C. Catal. Lett. 109 (2006) 171
60. Mispelaere-Canivet C., Spindler J.F., Perrio S., and Beslin P. Tetrahedron 61 (2005) 5253
61. Dickens M.J., Gilday J.P., Mowlem T.J., and Widdowson D.A. Tetrahedron 47 (1991) 8621
62. Ishiyama T., Mori M., Suzuki A., and Miyaura N. J. Organomet. Chem. 525 (1996) 225
63. Zheng N., McWilliams J.C., Fleitz F.J., Armstrong J.D., and Volante R.P. J. Org. Chem. 63 (1998) 9606
64. Migita T., Shimizu T., Asami Y., Shiobara J., Kato Y., and Kosugi M. Bull. Chem. Soc. Jpn. 53 (1980) 1385
65. Kosugi M., Ogata T., Terada M., Sano H., and Migita T. Bull. Chem. Soc. Jpn. 58 (1985) 3657
66. Mann G., Baranano D., Hartwig J.F., Rheingold A.L., and Guzei I.A. J. Am. Chem. Soc. 120 (1998) 9205
67. Fernández-Rodríguez M.A., Shen Q., and Hartwig J.F. Chem.-Eur. J. 12 (2006) 7782
68. Li G.Y. Angew. Chem., Int. Ed. 40 (2001) 1513
69. Itoh T., and Mase T. Org. Lett. 6 (2004) 4587
70. Murata M., and Buchwald S.L. Tetrahedron 60 (2004) 7397
71. Schopfer U., and Schlapbach A. Tetrahedron 57 (2001) 3069
72. Carril M., SanMartin R., and Dominguez E. Chem. Soc. Rev. 37 (2008) 639
73. Zhu D., Xu L., Wu F., and Wan B.S. Tetrahedron Lett. 47 (2006) 5781
74. Lindley J. Tetrahedron 40 (1984) 1433
75. Bates C.G., Gujadhur R.K., and Venkataraman D. Org. Lett. 4 (2002) 2803
76. Palomo C., Oiarbide M., López R., and Gómez-Bengoa E. Tetrahedron Lett. 41 (2002) 1283
77. Ley S.V., and Thomas A.W. Angew. Chem., Int. Ed. 42 (2003) 5400
78. Wu Y.-J., and He H. Synlett (2003) 1789
79. Bates C.G., Saejueng P., Doherty M.Q., and Venkataraman D. Org. Lett. 6 (2004) 5005
80. Deng W., Zou Y., Wang Y.-F., Liu L., and Guo Q.-X. Synlett (2004) 1254
81. Savarin C., Srogl J., and Liebeskind L.S. Org. Lett. 4 (2002) 4309
82. Herradura P.S., Pendola K.A., and Guy R.K. Org. Lett. 2 (2000) 2019
83. Chen Y.-J., and Chen H.-H. Org. Lett. 8 (2006) 5609
84. Adams R., and Ferretti A. J. Am. Chem. Soc. 81 (1959) 4927
85. Pinchart A., Dallaire C., and Gingras M. Tetrahedron Lett. 39 (1998) 543
86. Kwong F.Y., and Buchwald S.L. Org. Lett. 4 (2002) 3517
87. Gingras M., Pinchart A., and Dallaire C. Angew. Chem. 110 (1998) 3338
88. Gingras M., Pinchart A., Dallaire C., Mallah T., and Levillain E. Chem.-Eur. J. 10 (2004) 2895
89. Gingras M., Raimundo J.M., and Chabre Y.M. Angew. Chem., Int. Ed. 45 (2006) 1686
90. Van Bierbeek A., and Gingras M. Tetrahedron Lett. 39 (1998) 6283
91. Pinchart A., Dallaire C., Van Bierbeek A., and Gingras M. Tetrahedron Lett. 40 (1999) 5479
92. Tsuchida E., Yamamoto K., Oyaizu K., and Suzuki F. Macromolecules 28 (1995) 409
93. Menger F.M., and Azov V.A. J. Am. Chem. Soc. 124 (2002) 11159
94. Oyama T., and Chujo Y. Macromolecules 32 (1999) 7732
95. Allcock H.R., and Olmeijer D.L. Macromolecules 31 (1998) 8036
96. Klapars A., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 14844
97. Franke J., and Vögtle F. Tetrahedron Lett. 25 (1984) 3445
98. Kaplan M.L., and Reents Jr. W.D. Tetrahedron Lett. 23 (1982) 373
99. Petrillo G., Novi M., Garbarino G., and Filiberti M. Tetrahedron 45 (1989) 7411
100. Hsung R.P., Chidsey C.E.D., and Sita L.R. Organometallics 14 (1995) 4808
101. Barbieri G., Cinquini M., Colonna S., and Montanar F. J. Chem. Soc., C (1968) 659
102. Heck R.F. Palladium Reagents in Organic Synthesis (1985), Academic, New York, NY
103. Takahashi Y., Ito S., Sakai S., and Ishii Y. J. Chem. Soc., D (1970) 1065