Preparation of unsymmetrical biaryls via Ni- or Pd-catalyzed coupling of aryl chlorides with arylzincs

Tetrahedron Letters

Volumn 39, Issue 36, 1998, Pages 6441-6444

  Miller, Joseph A ^a   Farrell, Robert P ^a  

^a NZ Legacy LLC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE; NICKEL; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS;

EID: 0032171505     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01391-4     Document Type: Article

References (14)

1. 1. Negishi, E.; King. A. O.; Okukado, N. J. Org. Chem. 1977, 42, 1821.
2. 2. Stanforth, S. P. Tetrahedron 1998, 54, 263.
3. 3. Shirakawa, E.; Yamasaki, K.; Hiyama, T. J. Chem. Soc., Perkin Trans. I 1997, 2449.
4. 4. (a) Mitchell, M. B.; Wallbank, P. J. Tetrahedron Lett. 1991, 32, 2273.
5. (b) Ali, N. M.; McKillop, A.; Mitchell, M. B.; Rebelo, R. A.; Wallbank, P. J. Tetrahedron, 1992, 37, 8117.
6. (c) Saito, S.; Sakai, M.; Miyaura, N. Tetrahedron Lett. 1996, 37, 2993.
7. (d) Reetz, M. T.; Breinbauer, R.; Wanninger, K. Tetrahedron Lett. 1996, 37, 4499.
8. (e) Indolese, A. F. Tetrahedron Lett. 1997, 38, 3513.
9. (f) Shen, W. Tetrahedron Lett. 1997, 38, 5575.
10. (g) Saito, S.; Oh-tani, S.; Miyaura, N. J. Org. Chem. 1997, 62, 8024.
11. 5. Although the Ni-catalyzed coupling of PhZnCl with 1,8-dichloroanthracene has been reported previously, no benefit was gained from use of this phenyl zinc reagent compared with PhMgBr for the coupling reaction: House, H. O.; Ghali, N. I.; Haack, J. L.; VanDerveer, D. J. Org. Chem. 1980, 45, 1807.
12. 6. For a review on organozinc compounds in synthesis, see: Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.
13. 7. Representative procedure: [4-(4'-Methylphenyl)propiophenone; entry 6]. A solution of nickel acetylacetonate (0.128 g; 0.500 mmol; 5 mol%) and triphenylphosphine (0.523 g; 2.00 mmol; 20 mol%) in THF (5 mL) was treated with water (18 μL; 1.0 mmol; 10 mol%), cooled to 0° C, and further treated with Vitride (0,28 mL; 0.50 mmol; 5 mol%; 35 wt% in THF; ca 1.8 M). The dark reddish brown solution was stirred at 0° C for 10 min to complete the preparation of the nickel catalyst. In a separate flask, a solution of zinc chloride ( 1.77 g; 13.0 mmol) in THF (25 mL) was treated at 0° C with p-tolylmagnesium chloride (7.80 mL; 12.5 mmol; 1.60 M in THF), and the resulting mixture was warmed to room temperature and stirred for 15 min. The p-tolylzinc chloride obtained was treated at room temperature with the solution of nickel catalyst followed by 4-chloropropiophenone (1.68 g; 10.0 mmol). After stirring at room temperature for 1 h, a sample was withdrawn and quenched in a mixture of 1 N HCl and ether. GC analysis of the organic phase of the hydrolyzed reaction sample showed the presence of 8.5 mmol (85% yield) of 4-(4′-methylphenyl)propiophenone and no remaining 4-chloropropiophenone in the reaction mixture.
14. 8. H. Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445.