A synthesis of biaryls via nickel(0)-catalyzed cross-coupling reaction of chloroarenes with phenylboronic acids

Tetrahedron Letters

Volumn 37, Issue 17, 1996, Pages 2993-2996

  Saito, Syun ^a   Sakai, Masaaki ^a   Miyaura, Norio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029878151     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00482-0     Document Type: Article

References (15)

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2. (b) Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett. 1992, 207.
3. (c) For a review, see: Miyaura, N.; Suzuki, A. Chem. Res. 1995, 95, 2457.
4. Mitchell, M. B.; Wallbank, P. J. Tetrahedron Lett. 1991, 32, 2273. Ali, N. M.; McKillop, A.; Mitchell, M. B.; Rebelo, R. A.; Wallbank, P. J. Tetrahedron, 1992, 48, 8117. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry, 1993, 4, 743. Janietz, D.; Bauer, M. Synthesis 1993, 33. Achab, S.; Guyot, M.; Potier, P. Tetrahedron Lett. 1993, 34, 2127.
5. Mitchell, M. B.; Wallbank, P. J. Tetrahedron Lett. 1991, 32, 2273. Ali, N. M.; McKillop, A.; Mitchell, M. B.; Rebelo, R. A.; Wallbank, P. J. Tetrahedron, 1992, 48, 8117. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry, 1993, 4, 743. Janietz, D.; Bauer, M. Synthesis 1993, 33. Achab, S.; Guyot, M.; Potier, P. Tetrahedron Lett. 1993, 34, 2127.
6. Mitchell, M. B.; Wallbank, P. J. Tetrahedron Lett. 1991, 32, 2273. Ali, N. M.; McKillop, A.; Mitchell, M. B.; Rebelo, R. A.; Wallbank, P. J. Tetrahedron, 1992, 48, 8117. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry, 1993, 4, 743. Janietz, D.; Bauer, M. Synthesis 1993, 33. Achab, S.; Guyot, M.; Potier, P. Tetrahedron Lett. 1993, 34, 2127.
7. Mitchell, M. B.; Wallbank, P. J. Tetrahedron Lett. 1991, 32, 2273. Ali, N. M.; McKillop, A.; Mitchell, M. B.; Rebelo, R. A.; Wallbank, P. J. Tetrahedron, 1992, 48, 8117. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry, 1993, 4, 743. Janietz, D.; Bauer, M. Synthesis 1993, 33. Achab, S.; Guyot, M.; Potier, P. Tetrahedron Lett. 1993, 34, 2127.
8. Mitchell, M. B.; Wallbank, P. J. Tetrahedron Lett. 1991, 32, 2273. Ali, N. M.; McKillop, A.; Mitchell, M. B.; Rebelo, R. A.; Wallbank, P. J. Tetrahedron, 1992, 48, 8117. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry, 1993, 4, 743. Janietz, D.; Bauer, M. Synthesis 1993, 33. Achab, S.; Guyot, M.; Potier, P. Tetrahedron Lett. 1993, 34, 2127.
9. Tamao, K. Comprehensive Organic Synthesis, Trost, B. M.; Fleming, L; Pattenden, G., Eds.; Pergamon: New York, 1991; Vol. 3, p 435. Farina, V. Comprehensive Organometallic Chemistry II, Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: New York, 1995; Vol. 12, p 161.
10. Tamao, K. Comprehensive Organic Synthesis, Trost, B. M.; Fleming, L; Pattenden, G., Eds.; Pergamon: New York, 1991; Vol. 3, p 435. Farina, V. Comprehensive Organometallic Chemistry II, Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: New York, 1995; Vol. 12, p 161.
11. Percec, V.; Bae, J-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 1060.
12. 6
13. Morrell, D. G.; Kochi, J. K. J. Am. Chem. Soc. 1975, 97, 7262.
14. 1c
15. 3 gives a large Hammett's p value (8.8) for the electron-withdrawing substituents with σ > 0.23, but the electron-donating groups (σ < 0.23) indicates no difference in reactivity, see: Foá, M.; Cassar, L. J. Chem. Soc. Dalton Trans. 1975, 2572.