Homocoupling of Halotropones
REFERENCES
1599
1. Semmelhack, M. F.; Helquist, P. M.; Jones, L. D. Synthesis with zerovalent
nickel: Coupling of aryl halides with bis(1,5-cyclooctadiene) nickel(0). J. Am.
Chem.Soc. 1971, 93, 5908–5910.
´
2. Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Aryl-aryl bond
formation one century after the discovery of the Ullmann reaction. Chem.
Rev. 2002, 102, 1359–1469.
3. Kende, A. S.; Liebeskind, L. S.; Braitsch, D. M. In situ generation of a solvated
zero-valent nickel reagent: Biaryl formation. Tetrahedron Lett. 1975, 3375–3378.
4. Zembayashi, M.; Tamao, K.; Yoshida, J.-I; Kumada, M. Nickel-phosphine
complex–catalyzed homo coupling of aryl halides in the presence of zinc pow-
der. Tetrahedron Lett. 1977, 4089–4092.
5. Howarth, J.; James, P.; Dai, J. The coupling of aryl halides in the ionic liquid
[bmim]PF6. Tetrahedron Lett. 2000, 41, 10319–10321.
6. Iyoda, M.; Sato, K.; Oda, M. A. Simple synthesis of bitropones and conver-
sion of 2,20-bitropone into dicyclohepta[b,d]furan dication, a novel dication
species. Chem. Commun. 1985, 1547.
7. Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Homocoupling
of aryl halides using nickel(II) complex and zinc in the presence of Et4NI:
An efficient method for the synthesis of biaryls and bipyridines. Bull. Chem.
Soc. Jpn. 1990, 63, 80–87.
8. Alonso, F.; Riente, P.; Yus, M. Homocoupling of aryl iodides promoted by
nickel(0) nanoparticles. Arkivoc 2008, 4, 8–15.
9. Tao, X.-C.; Zhou, W.; Zhang, Y.-P.; Dai, C.-Y.; Shen, D.; Huang, M. Homo-
coupling of aryl bromides catalyzed by nickel chloride in pyridine. Chin. J.
Chem. 2006, 24, 939–942.
10. Colon, I.; Kelsey, D. R. Coupling of aryl chlorides by nickel and reducing
metals. J. Org. Chem. 1986, 51, 2627–2637.
11. Chen, C. NiCl2=CrCl2=Mn-mediated homocoupling of aryl halides accom-
plished in the presence of bipyridyl-type ligand. Synlett 2000, 1490–1492.
12. Zheng, X.; Zhang, Y. Coupling reaction of aryl halides promoted by
NiCl2=PPh3=Sm0. J. Chem. Res. 2002, 562–563.
13. Raynal, F.; Barhdadi, R.; Perichon, J.; Savall, A.; Troupel, M. Water as
solvent for nickel-2,20-bipirydine-catalysed electrosynthesis of biaryls from
haloaryls. Adv. Synth. Catal. 2002, 344, 45–49.
´ ´
14. Barhdadi, R.; Courtinard, C.; Nedelec, J. Y.; Troupel, M. Room-temperature
ionic liquids as new solvents for organic electrosynthesis: The first examples
of direct or nickel-catalysed electroreductive coupling involving organic
halides. Chem. Comm. 2003, 1434–1435.
15. Yamamoto, T.; Wakabayashi, S.; Osakada, K. Mechanism of C-C coupling
reactions of aromatic halides, promoted by Ni(COD)2 in the presence of 2,20-
bipyridine and PPh3, to give biaryls. J. Organomet.Chem. 1992, 428, 223–237.
16. Abla, M.; Yamamoto, T. Kinetic study of ligand exchange reactions of
bis(1,5-cyclooctadiene) nickel(0) with 2,20-bipyridine, 4,40-dimethyl-2,20-
bipyridine, and 4,40,5,50-tetramethyl-2,20-bipyridine. Bull. Chem. Soc. Jpn.
1999, 72, 1255–1261.