Selective Pd(0)-Catalyzed Arylations with New Electrophilic or Nucleophilic Multi-Coupling Reagents

Synlett

Volumn 1996, Issue 6, 1996, Pages 573-575

  Rottländer, Mario ^a   Palmer, Nick ^a   Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042270897     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5480     Document Type: Article

References (40)

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21. Hayashi, T., Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158. Hayashi, T.; Katsuro, Y.; Okamoto, Y.; Kumada, M. Tetrahedron Lett. 1981, 22, 4449. Hayashi, T.; Fujiwa, T.; Okamoto, Y.; Katsuro, Y.; Kumada, M. Synthesis 1981, 1001. Hayashi, T.; Katsuro, Y.; Kumada, M. Tetrahedron Lett. 1980, 21, 3915. Hayashi, T.; Konishi, M.; Yokota, K.; Kumada, M. Chem. Lett. 1980, 6, 767. Hayashi, T.; Konishi, M.; Yokata, K.-I.; Kumada, M. J. Organomet. Chem. 1985, 255, 359. The phosphine ddpf is conveniently prepared in high yield by using the excellent procedure of Brandsma; de Lang, R. J.; van Soolingen, J.; Verkruijsse, H. D.; Brandsma, L. Synth. Commun. 1995, 25, 2989.
22. Hayashi, T., Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158. Hayashi, T.; Katsuro, Y.; Okamoto, Y.; Kumada, M. Tetrahedron Lett. 1981, 22, 4449. Hayashi, T.; Fujiwa, T.; Okamoto, Y.; Katsuro, Y.; Kumada, M. Synthesis 1981, 1001. Hayashi, T.; Katsuro, Y.; Kumada, M. Tetrahedron Lett. 1980, 21, 3915. Hayashi, T.; Konishi, M.; Yokota, K.; Kumada, M. Chem. Lett. 1980, 6, 767. Hayashi, T.; Konishi, M.; Yokata, K.-I.; Kumada, M. J. Organomet. Chem. 1985, 255, 359. The phosphine ddpf is conveniently prepared in high yield by using the excellent procedure of Brandsma; de Lang, R. J.; van Soolingen, J.; Verkruijsse, H. D.; Brandsma, L. Synth. Commun. 1995, 25, 2989.
23. Hayashi, T., Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158. Hayashi, T.; Katsuro, Y.; Okamoto, Y.; Kumada, M. Tetrahedron Lett. 1981, 22, 4449. Hayashi, T.; Fujiwa, T.; Okamoto, Y.; Katsuro, Y.; Kumada, M. Synthesis 1981, 1001. Hayashi, T.; Katsuro, Y.; Kumada, M. Tetrahedron Lett. 1980, 21, 3915. Hayashi, T.; Konishi, M.; Yokota, K.; Kumada, M. Chem. Lett. 1980, 6, 767. Hayashi, T.; Konishi, M.; Yokata, K.-I.; Kumada, M. J. Organomet. Chem. 1985, 255, 359. The phosphine ddpf is conveniently prepared in high yield by using the excellent procedure of Brandsma; de Lang, R. J.; van Soolingen, J.; Verkruijsse, H. D.; Brandsma, L. Synth. Commun. 1995, 25, 2989.
24. Hayashi, T., Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158. Hayashi, T.; Katsuro, Y.; Okamoto, Y.; Kumada, M. Tetrahedron Lett. 1981, 22, 4449. Hayashi, T.; Fujiwa, T.; Okamoto, Y.; Katsuro, Y.; Kumada, M. Synthesis 1981, 1001. Hayashi, T.; Katsuro, Y.; Kumada, M. Tetrahedron Lett. 1980, 21, 3915. Hayashi, T.; Konishi, M.; Yokota, K.; Kumada, M. Chem. Lett. 1980, 6, 767. Hayashi, T.; Konishi, M.; Yokata, K.-I.; Kumada, M. J. Organomet. Chem. 1985, 255, 359. The phosphine ddpf is conveniently prepared in high yield by using the excellent procedure of Brandsma; de Lang, R. J.; van Soolingen, J.; Verkruijsse, H. D.; Brandsma, L. Synth. Commun. 1995, 25, 2989.
25. Hayashi, T., Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158. Hayashi, T.; Katsuro, Y.; Okamoto, Y.; Kumada, M. Tetrahedron Lett. 1981, 22, 4449. Hayashi, T.; Fujiwa, T.; Okamoto, Y.; Katsuro, Y.; Kumada, M. Synthesis 1981, 1001. Hayashi, T.; Katsuro, Y.; Kumada, M. Tetrahedron Lett. 1980, 21, 3915. Hayashi, T.; Konishi, M.; Yokota, K.; Kumada, M. Chem. Lett. 1980, 6, 767. Hayashi, T.; Konishi, M.; Yokata, K.-I.; Kumada, M. J. Organomet. Chem. 1985, 255, 359. The phosphine ddpf is conveniently prepared in high yield by using the excellent procedure of Brandsma; de Lang, R. J.; van Soolingen, J.; Verkruijsse, H. D.; Brandsma, L. Synth. Commun. 1995, 25, 2989.
26. Hayashi, T., Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158. Hayashi, T.; Katsuro, Y.; Okamoto, Y.; Kumada, M. Tetrahedron Lett. 1981, 22, 4449. Hayashi, T.; Fujiwa, T.; Okamoto, Y.; Katsuro, Y.; Kumada, M. Synthesis 1981, 1001. Hayashi, T.; Katsuro, Y.; Kumada, M. Tetrahedron Lett. 1980, 21, 3915. Hayashi, T.; Konishi, M.; Yokota, K.; Kumada, M. Chem. Lett. 1980, 6, 767. Hayashi, T.; Konishi, M.; Yokata, K.-I.; Kumada, M. J. Organomet. Chem. 1985, 255, 359. The phosphine ddpf is conveniently prepared in high yield by using the excellent procedure of Brandsma; de Lang, R. J.; van Soolingen, J.; Verkruijsse, H. D.; Brandsma, L. Synth. Commun. 1995, 25, 2989.
27. 4 as catalyst, however Pd(dppf) is the only catalyst which works generally well with all aryl triflates. See also: Koch, K.; Chambers, R. J.; Biggers, M. S. Synlett 1994, 347. Quesnelle, C. A.; Familari, O. B.; Snieckus, V. Synlett 1994, 349.
28. 4 as catalyst, however Pd(dppf) is the only catalyst which works generally well with all aryl triflates. See also: Koch, K.; Chambers, R. J.; Biggers, M. S. Synlett 1994, 347. Quesnelle, C. A.; Familari, O. B.; Snieckus, V. Synlett 1994, 349.
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39. 4. After concentration under vacuum the crude product was purified by flash chromatography with hexanes yielding the desired product 24 (907 mg, 81 %) as a colorless oil.
40. Ritter, K. Synthesis 1993, 735.