An iminophosphine-palladium catalyst for cross-coupling of aryl halides with organostannanes

Tetrahedron Letters

Volumn 38, Issue 21, 1997, Pages 3759-3762

  Shirakawa, Eiji ^a   Yoshida, Hiroto ^a   Takaya, Hidemasa ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030903044     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00747-8     Document Type: Article

References (19)

1. Kosugi, M.; Sasazawa, K.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 301-302.
2. For reviews, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
3. (b) Mitchell, T. N. Synthesis 1992, 803-815.
4. (c) Farina, V. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 3.4; pp 200-221.
5. Farina, V. Pure Appl. Chem. 1996, 68, 73-78.
6. Some transition metal complexes containing N-(2-diphenylphosphinobenzylidene)-alkyl-or arylamine have been used as catalysts for alkylation of allylic carboxylates, hydrogenation of olefins and hydrosilation of ketones. For examples, see: (a) Barbaro, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometallics 1995, 14, 5160-5170.
7. (b) Brunner, H.; Fürst, J. Inorg. Chim. Acta 1994, 220, 63-66.
8. (c) Brunner, H.; Rahman, A. F. M. M. Chem. Ber. 1984, 117, 710-724.
9. 24NP: C, 82.42; H, 6.15; N, 3.56. Found: C, 82.25; H, 6.19; N, 3.56. For the preparation of 2-diphenylphosphinobenzaldehyde, see: Rauchfuss, T. B.; Wrobleski, D. A. Inorg. Synth. 1982, 21, 175-179.
10. 3COOH as external standard) δ 13.6.
11. 3COOH as external standard) for 3a: δ 12.64; 5a: δ 12.85.
12. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
13. For the previous reports where the chelate coordination of P-N ligands to palladium(II) complexes are confirmed by X-ray diffraction studies.
14. (a) For the palladium(II) complexes with the iminophosphine, N-(2-diphenylphosphinobenzylidene)-(S)-1-phenylethylamine, which have similar structure to 1, see: Ankersmit, H. A.; Løken, B. H.; Kooijman, H.; Spek, A. L.; Vrieze, K.; van Koten, G. Inorg. Chim. Acta 1996, 252, 141-155.
15. (b) For the aminophosphine 2-palladium(II) complexes, see: de Graaf, W.; Harder, S.; Boersma, J.; van Koten, G.; Kanters, J. A. J. Organomet. Chem. 1988, 358, 545-562.
16. In the coupling of aryl halides with organostannanes, bidentate ligands have not been so frequently used as monodentate ligands. For examples of N-N ligands, see: (a) Wright, M. E.; Lowe-Ma, C. K. Organometallics 1990, 9, 347-352.
17. (b) Tamayo, N.; Echavarren, A. M.; Paredes, M. C.; Fariña, F.; Noheda, P. Tetrahedron Lett. 1990, 31, 5189-5192.
18. For examples of P-P ligands, see: (c) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992-4998.
19. (d) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033-3040. See, also reference 8.