The Application of Nickel(0) Catalyzed Homocoupling Reaction to the Synthesis of Novel 2,2'-Dipheny1-4,4'-dihydroxybipheny1

Jin-Young Bae; Virgil Percec

Journal of Industrial and Engineering Chemistry, Vol.4, No.1, 64-67, March, 1998

Jin-Young Bae , and Virgil Percec¹

Department of Polymer Science and Engineering, Sung Kyun Kwan University, Suwon 440-746, Korea
¹Department of Macromolecular Science, Case Western Reserve University, Cleveland, OH 44106-7202, USA

Nickel(0)-catalyzed homocoupling of aryl mesylate of 4-protected-2-substituted hydroquinone was utilized in the key step of the novel synthesis of 2,2'-diphenyl-4,4'-dihydroxybiphenyl. The synthetic procedure reported in this paper is of important value since it represents an easy and direct access to a wide variety of 2,2'-disubstituted-4,4'-dihydroxybiphenyls employing readily available hydroquinone derivatives as starting materials.

[References]

Heck RF, Palladium Reagents in Organic Synthesis; Academic Press: New York (1985)
Kumada M, Pure Appl. Chem., 52, 669 (1980)
Negishi E, Accounts Chem. Res., 20, 65 (1987)
Stille JK, Angew. Chem.-Int. Edit., 25, 508 (1986)
Suzuki A, Pure Appl. Chem., 57, 1749 (1985)
Casser L, J. Org. Chem., 93, 253 (1975)
Semmalhack MF, Helquist PM, Jones LD, J. Am. Chem. Soc., 93, 5908 (1971)
Percec V, Bae JY, Zhao M, Hill DH, J. Org. Chem., 60, 176 (1995)
Percec V, Bae JY, Zhao M, Hill DH, J. Org. Chem., 60, 1066 (1995)
Roger HG, Gaudiana RA, Minns RA, U.S. Patent, 4,433,132 (1984)
Roger HG, Gaudiana RA, Minns RA, Chem. Abstr., 100, 175562 (1984)
Schmitt HW, Guo D, Makromol. Chem., 189, 2029 (1988)
Kern W, Gruber W, Wirth HO, Makromol. Chem., 37, 198 (1960)
Perold GW, Afr JS, Chem. Inst., 28, 292 (1975)
Perold GW, Afr JS, Chem. Abstr., 85, 20739 (1976)
Tashiro M, Fukata G, Yamato T, Watanabe H, Oe K, Tsuge O, Org. Prep. Proced. Int., 8, 249 (1976)
Vauchier C, Vinet F, Maiser N, Liq. Cryst., 5, 141 (1989)
Vauchier C, Vinet F, Eur. Patent, 236,215 (1987)
Vauchier C, Vinet F, Chem. Abstr., 108, 104094 (1987)
Venanzi LM, J. Chem. Soc., 719 (1958)
Crossland RK, Servis KL, J. Org. Chem., 35, 3195 (1970)
Marrel DG, Kochi JK, J. Am. Chem. Soc., 97, 7262 (1975)
Colon I, Kelsey DR, J. Org. Chem., 51, 2627 (1986)

[Referenced By]

[Related Articles]

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

[2] Kumada M, Pure Appl. Chem., 52, 669 (1980)

[3] Negishi E, Accounts Chem. Res., 20, 65 (1987)

[4] Stille JK, Angew. Chem.-Int. Edit., 25, 508 (1986)

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

[6] Casser L, J. Org. Chem., 93, 253 (1975)

[7] Semmalhack MF, Helquist PM, Jones LD, J. Am. Chem. Soc., 93, 5908 (1971)

[8] Percec V, Bae JY, Zhao M, Hill DH, J. Org. Chem., 60, 176 (1995)

[9] Percec V, Bae JY, Zhao M, Hill DH, J. Org. Chem., 60, 1066 (1995)

[10] Roger HG, Gaudiana RA, Minns RA, U.S. Patent, 4,433,132 (1984)

[11] Roger HG, Gaudiana RA, Minns RA, Chem. Abstr., 100, 175562 (1984)

[12] Schmitt HW, Guo D, Makromol. Chem., 189, 2029 (1988)

[13] Kern W, Gruber W, Wirth HO, Makromol. Chem., 37, 198 (1960)

[14] Perold GW, Afr JS, Chem. Inst., 28, 292 (1975)

[15] Perold GW, Afr JS, Chem. Abstr., 85, 20739 (1976)

[16] Tashiro M, Fukata G, Yamato T, Watanabe H, Oe K, Tsuge O, Org. Prep. Proced. Int., 8, 249 (1976)

[17] Vauchier C, Vinet F, Maiser N, Liq. Cryst., 5, 141 (1989)

[18] Vauchier C, Vinet F, Eur. Patent, 236,215 (1987)

[19] Vauchier C, Vinet F, Chem. Abstr., 108, 104094 (1987)

[20] Venanzi LM, J. Chem. Soc., 719 (1958)

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

[22] Marrel DG, Kochi JK, J. Am. Chem. Soc., 97, 7262 (1975)

[23] Colon I, Kelsey DR, J. Org. Chem., 51, 2627 (1986)