Poly(p-phenylene)s via Pd(0) Catalyzed Cross-coupling of Arylene Bistriflate with Arylene Bisboronic Acid

Dong June Chung; jin-Young Bae

Journal of Industrial and Engineering Chemistry, Vol.5, No.4, 290-295, December, 1999

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Poly(p-phenylene)s via Pd(0) Catalyzed Cross-coupling of Arylene Bistriflate with Arylene Bisboronic Acid

Dong June Chung , and jin-Young Bae^†

Department of Polymer Science and Engineering, Sung Kyun Kwan University, Suwon 440-746, Korea

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This paper describes the synthesis and characterization of functional poly(p-phenylene)s (PPPs) based on palladium(0) catalyzed "Suzuki-type" cross-coupling reaction of aryl bistriflates derived from substituted hydroquinones with aryl bisboronic acids or its ester in the presence of a base. The effect of various reaction conditions such as palladium catalyst, solvent, base and additives on the reaction yield and the molecular weight of the polymer is discussed.

Keywords:poly(p-phemylene);transition metal;palladium catalyst;cross-coupling;aryl triflate

[References]

Suzuki A, Pure Appl. Chem., 57, 1749 (1985)
Ohe T, Miyaura N, Suzuki A, J. Org. Chem., 58, 2201 (1993)
Heck RF, Palladium Reagents in Organic Synthesis; Academic Press: New York (1985)
Noren GK, Stille JK, Macromol. Rev., 5, 385 (1971)
Percec V, Wang J, Okita S, Am. Chem. Soc. Dev. Polym. Chem. Polym. Prepr., 33, 225 (1992)
Rehn M, Schluter AD, Wegner G, Feast WJ, Polymer, 30, 1060 (1989)
Coulson DR, Inorg. Synth., 13, 121 (1972)
Hayashi T, Konishi M, Kobori Y, Kumada M, Higuchi Y, Hirotsu K, J. Am. Chem. Soc., 106, 158 (1984)
Hansen RL, U.S. Patent, 3,346,612 (1967)
Hansen RL, Chem. Abstr., 68(P), 21698c (1968)
Crossland RK, Servis KL, J. Org. Chem., 35, 3195 (1970)
Bean FR, Johnson JR, J. Am. Chem. Soc., 54, 4415 (1932)
Schlenk W, Ann., 386, 295 (1910)
Schlenk W, Chem. Abstr., 4, 4469 (1910)
Procedure for the Synthesis was Applied: A.I. Vogel, Vogel's Textbook of Practical Organic Chemistry, 5th ed., p. 694, Longman, Harlow, U.K. (1989)
Chen QY, Yang Z, Tetrahedron Lett., 1171 (1986)
Coutts GC, Goldschmid HR, Musgrave, J. Chem. Soc.(C), 488 (1970)

[Referenced By]

[Related Articles]

[1] Suzuki A, Pure Appl. Chem., 57, 1749 (1985)

[2] Ohe T, Miyaura N, Suzuki A, J. Org. Chem., 58, 2201 (1993)

[3] Heck RF, Palladium Reagents in Organic Synthesis; Academic Press: New York (1985)

[4] Noren GK, Stille JK, Macromol. Rev., 5, 385 (1971)

[5] Percec V, Wang J, Okita S, Am. Chem. Soc. Dev. Polym. Chem. Polym. Prepr., 33, 225 (1992)

[6] Rehn M, Schluter AD, Wegner G, Feast WJ, Polymer, 30, 1060 (1989)

[7] Coulson DR, Inorg. Synth., 13, 121 (1972)

[8] Hayashi T, Konishi M, Kobori Y, Kumada M, Higuchi Y, Hirotsu K, J. Am. Chem. Soc., 106, 158 (1984)

[9] Hansen RL, U.S. Patent, 3,346,612 (1967)

[10] Hansen RL, Chem. Abstr., 68(P), 21698c (1968)

[11] Crossland RK, Servis KL, J. Org. Chem., 35, 3195 (1970)

[12] Bean FR, Johnson JR, J. Am. Chem. Soc., 54, 4415 (1932)

[13] Schlenk W, Ann., 386, 295 (1910)

[14] Schlenk W, Chem. Abstr., 4, 4469 (1910)

[15] Procedure for the Synthesis was Applied: A.I. Vogel, Vogel's Textbook of Practical Organic Chemistry, 5th ed., p. 694, Longman, Harlow, U.K. (1989)

[16] Chen QY, Yang Z, Tetrahedron Lett., 1171 (1986)

[17] Coutts GC, Goldschmid HR, Musgrave, J. Chem. Soc.(C), 488 (1970)