Nickel-catalyzed cross-couplings of unactivated alkyl halides and pseudohalides with organometallic compounds

Advanced Synthesis and Catalysis

Volumn 346, Issue 13-15, 2004, Pages 1525-1532

  Netherton, Matthew R ^a   Fu, Gregory C ^b  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Alkyl halides; C C coupling; Homogeneous catalysis; Nickel; Synthetic methods

Indexed keywords

ALKYL GROUP; HALIDE; NICKEL COMPLEX;

CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; GRIGNARD REACTION; HYDROGEN BOND; PERCEPTION; REVIEW; SUZUKI REACTION;

EID: 12344251733     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404223     Document Type: Review

References (49)

1. For reviews of metal-catalyzed cross-couplings, see: a) Metal-Catalyzed Cross-Coupling Reactions, (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, New York, 2004; b) Cross-Coupling Reactions: A Practical Guide, (Ed.: N. Miyaura), Topics in Current Chemistry Series 219, Springer-Verlag, New York, 2002; c) Handbook of Organopalladium Chemistry for Organic Synthesis, (Ed.: E.-i. Negishi), Wiley-Interscience, New York, 2002.
2. For reviews of metal-catalyzed cross-couplings, see: a) Metal-Catalyzed Cross-Coupling Reactions, (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, New York, 2004; b) Cross-Coupling Reactions: A Practical Guide, (Ed.: N. Miyaura), Topics in Current Chemistry Series 219, Springer-Verlag, New York, 2002; c) Handbook of Organopalladium Chemistry for Organic Synthesis, (Ed.: E.-i. Negishi), Wiley-Interscience, New York, 2002.
3. For reviews of metal-catalyzed cross-couplings, see: a) Metal-Catalyzed Cross-Coupling Reactions, (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, New York, 2004; b) Cross-Coupling Reactions: A Practical Guide, (Ed.: N. Miyaura), Topics in Current Chemistry Series 219, Springer-Verlag, New York, 2002; c) Handbook of Organopalladium Chemistry for Organic Synthesis, (Ed.: E.-i. Negishi), Wiley-Interscience, New York, 2002.
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8. Couplings with organoboron compounds: a) M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099-10100; b) J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 1945-1947; c) M. R. Netherton, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 3910-3912; d) J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; e) K. Arentsen, S. Caddick, F. G. N. Cloke, A. P. Herring, P. B. Hitchcock, Tetrahedron Lett. 2004, 45, 3511-3515.
9. Couplings with organoboron compounds: a) M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099-10100; b) J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 1945-1947; c) M. R. Netherton, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 3910-3912; d) J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; e) K. Arentsen, S. Caddick, F. G. N. Cloke, A. P. Herring, P. B. Hitchcock, Tetrahedron Lett. 2004, 45, 3511-3515.
10. Couplings with organoboron compounds: a) M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099-10100; b) J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 1945-1947; c) M. R. Netherton, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 3910-3912; d) J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; e) K. Arentsen, S. Caddick, F. G. N. Cloke, A. P. Herring, P. B. Hitchcock, Tetrahedron Lett. 2004, 45, 3511-3515.
11. Couplings with organoboron compounds: a) M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099-10100; b) J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 1945-1947; c) M. R. Netherton, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 39 10-3912; d) J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; e) K. Arentsen, S. Caddick, F. G. N. Cloke, A. P. Herring, P. B. Hitchcock, Tetrahedron Lett. 2004, 45, 3511-3515.
12. Couplings with organoboron compounds: a) M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099-10100; b) J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 1945-1947; c) M. R. Netherton, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 39 10-3912; d) J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; e) K. Arentsen, S. Caddick, F. G. N. Cloke, A. P. Herring, P. B. Hitchcock, Tetrahedron Lett. 2004, 45, 3511-3515.
13. Couplings with organomagnesium and organolithium compounds: a) A. C. Frisch, N. Shaikh, A. Zapf, M. Beller, Angew. Chem. Int. Ed. 2002, 41, 4056-4059; b) A. C. Frisch, F. Rataboul, A. Zapf, M. Beller, J. Organomet. Chem. 2003, 687, 403-409; c) J. Terao, Y. Naitoh, H. Kuniyasu, N. Kambe, Chem. Lett. 2003, 32, 890-891; d) L.-M. Yang, L.-F. Huang, T.-Y. Luh, Org. Lett. 2004, 6, 1461-1463.
14. Couplings with organomagnesium and organolithium compounds: a) A. C. Frisch, N. Shaikh, A. Zapf, M. Beller, Angew. Chem. Int. Ed. 2002, 41, 4056-4059; b) A. C. Frisch, F. Rataboul, A. Zapf, M. Beller, J. Organomet. Chem. 2003, 687, 403-409; c) J. Terao, Y. Naitoh, H. Kuniyasu, N. Kambe, Chem. Lett. 2003, 32, 890-891; d) L.-M. Yang, L.-F. Huang, T.-Y. Luh, Org. Lett. 2004, 6, 1461-1463.
15. Couplings with organomagnesium and organolithium compounds: a) A. C. Frisch, N. Shaikh, A. Zapf, M. Beller, Angew. Chem. Int. Ed. 2002, 41, 4056-4059; b) A. C. Frisch, F. Rataboul, A. Zapf, M. Beller, J. Organomet. Chem. 2003, 687, 403-409; c) J. Terao, Y. Naitoh, H. Kuniyasu, N. Kambe, Chem. Lett. 2003, 32, 890-891; d) L.-M. Yang, L.-F. Huang, T.-Y. Luh, Org. Lett. 2004, 6, 1461-1463.
16. Couplings with organomagnesium and organolithium compounds: a) A. C. Frisch, N. Shaikh, A. Zapf, M. Beller, Angew. Chem. Int. Ed. 2002, 41, 4056-4059; b) A. C. Frisch, F. Rataboul, A. Zapf, M. Beller, J. Organomet. Chem. 2003, 687, 403-409; c) J. Terao, Y. Naitoh, H. Kuniyasu, N. Kambe, Chem. Lett. 2003, 32, 890-891; d) L.-M. Yang, L.-F. Huang, T.-Y. Luh, Org. Lett. 2004, 6, 1461-1463.
17. Couplings with organozinc compounds: J. Zhou, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 12527-12530.
18. Couplings with organotin compounds: a) K. Menzel, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 3718-3719; b) H. Tang, K. Menzel, G. C. Fu, Angew. Chem. Int. Ed. 2003, 42, 5079-5082.
19. Couplings with organotin compounds: a) K. Menzel, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 3718-3719; b) H. Tang, K. Menzel, G. C. Fu, Angew. Chem. Int. Ed. 2003, 42, 5079-5082.
20. Couplings with organosilicon compounds: J.-Y. Lee, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 5616-5617.
21. Sonogashira reactions: M. Eckhardt, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 13642-13643.
22. Couplings with organozirconium compounds: S. L. Wiskur, A. Korte, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 82-83.
23. Copper-catalyzed processes: a) M. Tamura, J. Kochi, Synthesis 1971, 303-305; b) M. Tamura, J. K. Kochi, J. Organomet. Chem. 1972, 42, 205-228; c) J. Terao, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2003, 125, 5646-5647; d) J. G. Donkervoort, J. L. Vicario, J. T. B. H. Jastrzebski, R. A. Gossage, G. Cahiez, G. van Koten, J. Organomet. Chem. 1998, 558, 61-69; e) for additional leading references, see: B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631.
24. Copper-catalyzed processes: a) M. Tamura, J. Kochi, Synthesis 1971, 303-305; b) M. Tamura, J. K. Kochi, J. Organomet. Chem. 1972, 42, 205-228; c) J. Terao, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2003, 125, 5646-5647; d) J. G. Donkervoort, J. L. Vicario, J. T. B. H. Jastrzebski, R. A. Gossage, G. Cahiez, G. van Koten, J. Organomet. Chem. 1998, 558, 61-69; e) for additional leading references, see: B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631.
25. Copper-catalyzed processes: a) M. Tamura, J. Kochi, Synthesis 1971, 303-305; b) M. Tamura, J. K. Kochi, J. Organomet. Chem. 1972, 42, 205-228; c) J. Terao, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2003, 125, 5646-5647; d) J. G. Donkervoort, J. L. Vicario, J. T. B. H. Jastrzebski, R. A. Gossage, G. Cahiez, G. van Koten, J. Organomet. Chem. 1998, 558, 61-69; e) for additional leading references, see: B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631.
26. Copper-catalyzed processes: a) M. Tamura, J. Kochi, Synthesis 1971, 303-305; b) M. Tamura, J. K. Kochi, J. Organomet. Chem. 1972, 42, 205-228; c) J. Terao, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2003, 125, 5646-5647; d) J. G. Donkervoort, J. L. Vicario, J. T. B. H. Jastrzebski, R. A. Gossage, G. Cahiez, G. van Koten, J. Organomet. Chem. 1998, 558, 61-69; e) for additional leading references, see: B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631.
27. Copper-catalyzed processes: a) M. Tamura, J. Kochi, Synthesis 1971, 303-305; b) M. Tamura, J. K. Kochi, J. Organomet. Chem. 1972, 42, 205-228; c) J. Terao, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2003, 125, 5646-5647; d) J. G. Donkervoort, J. L. Vicario, J. T. B. H. Jastrzebski, R. A. Gossage, G. Cahiez, G. van Koten, J. Organomet. Chem. 1998, 558, 61-69; e) for additional leading references, see: B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631.
28. Iron-catalyzed processes: a) U. H. Brinker, L. König, Chem. Ber. 1983, 116, 882-893; b) M. Nakamura, K. Matsuo, S. Ito, E. Nakamura, J. Am. Chem. Soc. 2004, 126, 3686-3687; c) T. Nagano, T. Hayashi, Org. Lett, 2004, 6, 1297-1299; d) R. Martin, A. Fürstner, Angew. Chem. Int. Ed. 2004, 43, 3955-3957.
29. Iron-catalyzed processes: a) U. H. Brinker, L. König, Chem. Ber. 1983, 116, 882-893; b) M. Nakamura, K. Matsuo, S. Ito, E. Nakamura, J. Am. Chem. Soc. 2004, 126, 3686-3687; c) T. Nagano, T. Hayashi, Org. Lett, 2004, 6, 1297-1299; d) R. Martin, A. Fürstner, Angew. Chem. Int. Ed. 2004, 43, 3955-3957.
30. Iron-catalyzed processes: a) U. H. Brinker, L. König, Chem. Ber. 1983, 116, 882-893; b) M. Nakamura, K. Matsuo, S. Ito, E. Nakamura, J. Am. Chem. Soc. 2004, 126, 3686-3687; c) T. Nagano, T. Hayashi, Org. Lett, 2004, 6, 1297-1299; d) R. Martin, A. Fürstner, Angew. Chem. Int. Ed. 2004, 43, 3955-3957.
31. Iron-catalyzed processes: a) U. H. Brinker, L. König, Chem. Ber. 1983, 116, 882-893; b) M. Nakamura, K. Matsuo, S. Ito, E. Nakamura, J. Am. Chem. Soc. 2004, 126, 3686-3687; c) T. Nagano, T. Hayashi, Org. Lett, 2004, 6, 1297-1299; d) R. Martin, A. Fürstner, Angew. Chem. Int. Ed. 2004, 43, 3955-3957.
32. Cobalt-catalyzed processes: T. Tsuji, H. Yorimitsu, K. Oshima, Angew. Chem. Int. Ed. 2002, 41, 4137-4139.
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41. J. Zhou, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 1340-1341.
42. For an interesting recent study that suggests the involvement of a Ni(I) intermediate in Negishi cross-couplings of alkyl iodides, see: T. J. Anderson, G. D. Jones, D. A. Vicic, J. Am. Chem. Soc. 2004, 120, 8100-8101.
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44. [4c]
45. [4c]
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48. J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222-4223.
49. [12d]