Homocoupling of substituted benzenes to symmetrical biaryls is achieved with different cerium(IV) compounds such as cerium(IV) triethylammonium nitrate (CTEAN), cerium(IV) pyridinium nitrate (CPN) and Ce(OTf)4 in the presence of HgII in good to high yields.
References
1.
For a review see, SainsburyM., Tetrahedron, 1980, 36, 3327.
2.
SolladleG., and GottarelliG., Tetrahedron, 1987, 43, 1425; G. W. Gray, Molecular Structures and the Properties of Liquid Crystals, Academic Press, London, 1962.
3.
AntoneU., GoeltnerC., and MuellenK., Chem. Ber., 1992, 125, 2325.
4.
FanatP. E., Chem. Rev., 1964, 64, 613.
5.
DermerO. C., and EdmisonM. T., Chem. Rev., 1957, 57, 77.
6.
EisomL. F., HuntJ. D., and MackillopA., Organomet. Chem. Rev., Sect. A, 1972, 8, 135.
7.
(a) McKillopA., TurrellA. G., YoungD. W., and TaylorE. C., J. Am. Chem. Soc., 1980, 102, 6504; (b) A. D. Ryabov, S. A. Deiko, A. K. Yatsimirsky and I. V. Berezin, Tetrahedron Lett., 1981, 22, 3793.
8.
(a) For a review see, KozhenvikovI. V., and MatveevK. I., Usp. Khim.(Russ.), 1978, 47, 1231; (b) M. O. Unger and R. A. Fouty, J. Org. Chem., 1968, 34, 18; (c) D. H. R. Barton, N. Ozbalik and M. Ramesh, Tetrahedron, 1988, 44, 5661.
9.
LourakM., VanderesseR., FortY., and CaubereP., J. Org. Chem., 1989, 54, 4840; M. Iyoda, H. Otsuka, K. Sato, N. Nisato and M. Oda, Bull. Chem. Soc. Jpn., 1990, 63, 80.
10.
YamashitaJ., InoueY., KondoT., and HashimotoH., Chem. Lett., 1986, 407.
11.
JutandA., and MoslehA., Synlett, 1993, 569.
12.
MiuraM., HashimotoH., ItohK., and NomuraM., Chem. Lett., 1990, 459.
13.
KangS. K., NamkoongE. Y., and YamagichiT., Synth. Commun., 1997, 27, 641.
14.
KangS. K., ShivkumarU., AhnC., Sang-Chul ChoiC. A., and KimJ. S., Synth. Commun., 1997, 27, 1893.
15.
KangS. K., RyuH. C., and SonH. J., Synlett, 1997, 771.
16.
SmithJ. C., Synthesis, 1984, 629.
17.
FirouzabadiH., and IranpoorN., Synth. Commun., 1983, 13, 1143.
18.
(a) FirouzabadiH., IranpoorN., HajipoorG.H., KiaeezadehF., RazeeS., and ToofanJ., Iran J. Sci. Technol., 1987, 11, 246; (b) N. Iranpoor and J. Owji, Tetrahedron, 1991, 47, 149.
19.
IranpoorN., and ShekarrizeM., Synth. Commun., 1998, 28, 347.