Homocoupling of Organostannanes Catalyzed by Iminophosphine-Palladium

Synlett

Volumn 1997, Issue 10, 1997, Pages 1143-1144

  Shirakawa, Eiji ^a   Murota, Yasubumi ^a   Nakao, Yoshiaki ^a   Hiyama, Tamejiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001728420     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-997     Document Type: Article

References (14)

1. Kosugi, M.; Sasazawa, K.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 301.
2. For reviews, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Mitchell, T. N. Synthesis 1992, 803. (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; p 200.
3. For reviews, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Mitchell, T. N. Synthesis 1992, 803. (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; p 200.
4. For reviews, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Mitchell, T. N. Synthesis 1992, 803. (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; p 200.
5. Stoichiometric amount of Copper(II) nitrate is shown to mediate the homocoupling of organostannanes. Ghosal, S.; Luke, G. P.; Kyler, K. S. J. Org. Chem. 1987, 52, 4296.
6. Although the homocoupling reaction of organostannanes is recorded in some papers, the products are deemed to be the side products of the corresponding cross-coupling reaction with aryl halides. For example, see: (a) Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434. (b) van Asselt, R.; Elsvier, C. J. Organometallics 1994, 13, 1972.
7. Although the homocoupling reaction of organostannanes is recorded in some papers, the products are deemed to be the side products of the corresponding cross-coupling reaction with aryl halides. For example, see: (a) Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434. (b) van Asselt, R.; Elsvier, C. J. Organometallics 1994, 13, 1972.
8. Kanemoto, S.; Matsubara, S.; Oshima, K.; Utimoto, K.; Nozaki, H. Chem. Lett. 1987, 5.
9. Liebeskind, L. S.; Riesinger, S. W. Tetrahedron Lett. 1991, 32, 5681.
10. Kang, S.-K.; Namkoong, E.-Y.; Yamaguchi, T. Synth. Commun. 1997, 27, 641.
11. Tolstikov, G. A.; Miftakhov, M. S.; Danilova, N. A.; Vel'der, Y. L.; Spirikhin, L. V. Synthesis 1989, 633.
12. We have already reported that the palladium complex coordinated by iminophosphine 4 is an efficient catalyst for the coupling of organostannanes with aryl halides. Shirakawa, E.; Yoshida, H.; Takaya, H. Tetrahedron Lett. 1997, 38, 3759.
13. In the copper(I)-promoted homocoupling of organosilanes, N,N-dimethylformamide was used as an effective solvent. Ikegashira, K; Nishihara, Y.; Hirabayashi, K.; Mori, A.; Hiyama, T. Chem. Commun. 1997, 1039.
14. 2 (3.0 mg, 0.008 mmol) in DMF (2 ml), and the resulting mixture was stirred at the temperature for the time both indicated in Table 2. Quenching with water (10 mL), extraction with ethyl acetate (30 mL X 2), washing the combined organic layer with water (10 mL) and brine (10 mL), drying the organic layer over anhydrous magnesium sulfate, and evaporation, followed by gel permeation chromatography, gave the corresponding coupling product. The yields are listed in Table 2.