Palladium-catalyzed three-component coupling: Polymerization of diyne, aryl dihalide, and hydride

Polymer Bulletin

Volumn 39, Issue 6, 1997, Pages 677-684

  Miyaki, Nobuyuki ^a   Tomita, Ikuyoshi ^a   Endo, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001715521     PISSN: 01700839     EISSN: None     Source Type: Journal    
DOI: 10.1007/s002890050202     Document Type: Article

References (26)

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5. (e) Chujo Y, Tomita I, Saegusa T (1992) Polym Bull 27: 375
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7. (g) Kuroda H, Tomita I, Endo T (1995) Macromolecules 28: 6020
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9. (b) idem (1997) J Polym Sci: Part A: Polym Chem 35: 1211
10. (c) idem (1997) J Polym Sci: Part A: Polym Chem 35: 2097
11. (d) idem (1997) Chem Lett 685
12. (e) idem (1997) Macromolecules 30: 4504
13. (a) Perlmutter P (1992) Conjugate Addition Reaction in Organic Synthesis. Pergamon: Oxford
14. (b) Trost BM (1991) Comprehensive Organic Synthesis Vol. 4. Pergamon: Oxford
15. (a) Cacchi S, Flelici M, Pietroni B (1984) Tetrahedron Lett 25: 3137
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19. (e) Arcadi A, Bernocchi E, Burini A, Cacchi S, Marinelli F, Pietroni B (1989) Tetrahedron Lett 30: 3465
20. In the case of the reaction with 3b, the starting material (i.e., 1,2-diphenylethylene) was recovered in 61 % yield.
21. Trost BM (1977) Tetrahedron 33: 2615
22. For the review related to the mechanisms on the Pd-catalyzed reactions, see: (a) Ram S, Ehrenkaufer RE (1988) Synthesis 91 (b) Tsuji J, Shimizu I (1990) J Synth Org Chem Jpn 48: 1016
23. For the review related to the mechanisms on the Pd-catalyzed reactions, see: (a) Ram S, Ehrenkaufer RE (1988) Synthesis 91 (b) Tsuji J, Shimizu I (1990) J Synth Org Chem Jpn 48: 1016
24. A white powdery polymer could be isolated when the polymer was purified further by HPLC. Thus, the pale yellow color observed for the polymer after precipitation is originated from any contaminants (e.g., the palladium catalyst).
25. 1H-NMR spectrum might be attributed to the protons in the diene unit produced by the double insertion of the acetylene moieties. From the detailed analysis of the minor products in the model reaction of 1,2-diphenylacetylene, p-iodotoluene, and sodium diethyl benzylmalonate (3a), as described above, 1-p-tolyl-1,2,3,4-tetraphenyl-1,3-butadiene (i.e., a double insertion product of the acetylene to the arylpalladium species) was isolated in 19 % yield (based on 1,2-diphenylacetylene) beside the major product. Although this result indicates the presence of the branched unit in 5a by means of the double insertion of the acetylene moieties, no gelation was observed unless the polymerization was carried out with an excess amount of the diyne.
26. The double insertion process was detected as a side reaction in the model experiment. See, ref. (8).