Suzuki-type coupling of chloroarenes with arylboronic acids catalysed by nickel complexes

Tetrahedron Letters

Volumn 38, Issue 20, 1997, Pages 3513-3516

  Indolese, Adriano F ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE; ORGANOCHLORINE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030921405     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00707-7     Document Type: Article

References (13)

1. (a) N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 1981, 11, 513. (b) For a review:
2. (a) For a review: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
3. (b) Martin, A.R.; Yang, Y. Acta Chem. Scand. 1993, 47, 221.
4. Mitchell, M.B.; Wallbank, P.J. Tetrahedron Lett. 1991, 32, 2273.
5. Grushin, V.V.; Alper, H. Chem. Rev. 1994, 94, 1047.
6. Percec, V.; Bae, J-Y.; Hill, D.H. J. Org. Chem. 1995, 60, 1060.
7. Saito, S.; Sakai, M.; Miyaura, N. Tetrahedron Lett. 1996, 37, 2993.
8. 3) gave yields below 10 %. K-t-butylate and tributylamine were completely ineffective. We can not excluded that an other base in combination with an other solvent than anisole might be suitable as well.
9. Cassar, L.; Ferrara, S.; Foà, M. "Homogenous Catalyis II", Adv. Chem. Ser. 132; Am. Chem. Soc. (1974); p. 252.
10. Cassar, L.; Ferrara, S.; Foà, M. "Homogenous Catalyis II", Adv. Chem. Ser. 132; Am. Chem. Soc. (1974); p. 252.
11. Moreno-Mañas, M.; Pérez, M.; Pleixats R. J. Org. Chem. 1996, 61, 2346.
12. Kong, K.C.; Cheng, H. J. Am. Chem. Soc. 1991, 113, 6313.
13. 4 (3 mmol) and phenylboronic acid (1.1 mmol) under argon 4-chloro-anisole (1 mmol) and degassed dioxane (4 ml) were added. The reaction mixture was stirred at 95 °C overnight. Water was added and the product was extracted with ether and purified by distillation. The products were identified by NMR spectroscopy.