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Volumn 62, Issue 23, 1997, Pages 8024-8030

Synthesis of Biaryls via a Nickel(0)-Catalyzed Cross-Coupling Reaction of Chloroarenes with Arylboronic Acids

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EID: 0000728442     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9707848     Document Type: Article
Times cited : (275)

References (67)
  • 1
    • 0012397313 scopus 로고    scopus 로고
    • For reviews: (a) Snieckus, V. Chem. Rev. 1990, 90, 879-939. (b) Martin, A. R.; Yang, Y. Acta. Chem. Scand. 1993, 47, 221-230. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (d) Miyaura, N. Fine Chemical 1997, 26(6), 5-15 and 26(7), 13-26.
    • (1990) Chem. Rev. , vol.90 , pp. 879-939
    • Snieckus, V.1
  • 2
    • 0012397313 scopus 로고    scopus 로고
    • For reviews: (a) Snieckus, V. Chem. Rev. 1990, 90, 879-939. (b) Martin, A. R.; Yang, Y. Acta. Chem. Scand. 1993, 47, 221-230. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (d) Miyaura, N. Fine Chemical 1997, 26(6), 5-15 and 26(7), 13-26.
    • (1993) Acta. Chem. Scand. , vol.47 , pp. 221-230
    • Martin, A.R.1    Yang, Y.2
  • 3
    • 2042507954 scopus 로고
    • For reviews: (a) Snieckus, V. Chem. Rev. 1990, 90, 879-939. (b) Martin, A. R.; Yang, Y. Acta. Chem. Scand. 1993, 47, 221-230. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (d) Miyaura, N. Fine Chemical 1997, 26(6), 5-15 and 26(7), 13-26.
    • (1995) Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 4
    • 0012397313 scopus 로고    scopus 로고
    • For reviews: (a) Snieckus, V. Chem. Rev. 1990, 90, 879-939. (b) Martin, A. R.; Yang, Y. Acta. Chem. Scand. 1993, 47, 221-230. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (d) Miyaura, N. Fine Chemical 1997, 26(6), 5-15 and 26(7), 13-26.
    • (1997) Fine Chemical , vol.26 , Issue.6 , pp. 5-15
    • Miyaura, N.1
  • 5
    • 0012397313 scopus 로고    scopus 로고
    • For reviews: (a) Snieckus, V. Chem. Rev. 1990, 90, 879-939. (b) Martin, A. R.; Yang, Y. Acta. Chem. Scand. 1993, 47, 221-230. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (d) Miyaura, N. Fine Chemical 1997, 26(6), 5-15 and 26(7), 13-26.
    • Fine Chemical , vol.26 , Issue.7 , pp. 13-26
  • 12
    • 0025822505 scopus 로고
    • Mitchell, M. B.; Wallbank, P. J. Tetrahedron Lett. 1991, 32, 2273-2276. Ali, N. M.; McKillop, A.; Mitchell, M. B.; Rebelo, R. A.; Wallbank, P. J. Tetrahedron 1992, 48, 8117-8126. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743. Janietz, D.; Bauer, M. Synthesis 1993, 33-34. Achab, S.; Guyot, M.; Potier, P. Tetrahedron Lett. 1993, 34, 2127-2130.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 2273-2276
    • Mitchell, M.B.1    Wallbank, P.J.2
  • 13
    • 0026780035 scopus 로고
    • Mitchell, M. B.; Wallbank, P. J. Tetrahedron Lett. 1991, 32, 2273-2276. Ali, N. M.; McKillop, A.; Mitchell, M. B.; Rebelo, R. A.; Wallbank, P. J. Tetrahedron 1992, 48, 8117-8126. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743. Janietz, D.; Bauer, M. Synthesis 1993, 33-34. Achab, S.; Guyot, M.; Potier, P. Tetrahedron Lett. 1993, 34, 2127-2130.
    • (1992) Tetrahedron , vol.48 , pp. 8117-8126
    • Ali, N.M.1    McKillop, A.2    Mitchell, M.B.3    Rebelo, R.A.4    Wallbank, P.J.5
  • 14
    • 0027408256 scopus 로고
    • Mitchell, M. B.; Wallbank, P. J. Tetrahedron Lett. 1991, 32, 2273-2276. Ali, N. M.; McKillop, A.; Mitchell, M. B.; Rebelo, R. A.; Wallbank, P. J. Tetrahedron 1992, 48, 8117-8126. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743. Janietz, D.; Bauer, M. Synthesis 1993, 33-34. Achab, S.; Guyot, M.; Potier, P. Tetrahedron Lett. 1993, 34, 2127-2130.
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 743
    • Alcock, N.W.1    Brown, J.M.2    Hulmes, D.I.3
  • 15
    • 0027399876 scopus 로고
    • Mitchell, M. B.; Wallbank, P. J. Tetrahedron Lett. 1991, 32, 2273-2276. Ali, N. M.; McKillop, A.; Mitchell, M. B.; Rebelo, R. A.; Wallbank, P. J. Tetrahedron 1992, 48, 8117-8126. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743. Janietz, D.; Bauer, M. Synthesis 1993, 33-34. Achab, S.; Guyot, M.; Potier, P. Tetrahedron Lett. 1993, 34, 2127-2130.
    • (1993) Synthesis , pp. 33-34
    • Janietz, D.1    Bauer, M.2
  • 16
    • 0027406260 scopus 로고
    • Mitchell, M. B.; Wallbank, P. J. Tetrahedron Lett. 1991, 32, 2273-2276. Ali, N. M.; McKillop, A.; Mitchell, M. B.; Rebelo, R. A.; Wallbank, P. J. Tetrahedron 1992, 48, 8117-8126. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743. Janietz, D.; Bauer, M. Synthesis 1993, 33-34. Achab, S.; Guyot, M.; Potier, P. Tetrahedron Lett. 1993, 34, 2127-2130.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 2127-2130
    • Achab, S.1    Guyot, M.2    Potier, P.3
  • 18
    • 0001492945 scopus 로고    scopus 로고
    • Uemura, M.; Nishimura, H.; Kamikawa, K.; Nakayama, K.; Hayashi, Y.; Tetrahedron Lett. 1994, 35, 1905-1908. Kamiyama, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375.
    • (1996) J. Org. Chem. , vol.61 , pp. 1375
    • Kamiyama, K.1    Watanabe, T.2    Uemura, M.3
  • 27
    • 0001538227 scopus 로고
    • Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon: New York
    • For reviews, see: (c) Tamao, K. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon: New York, 1991; Vol. 3, p 435. (d) 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.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 435
    • Tamao, K.1
  • 28
    • 0001186913 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus, L. S., Eds.; Pergamon: New York
    • For reviews, see: (c) Tamao, K. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon: New York, 1991; Vol. 3, p 435. (d) 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.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 161
    • Farina, V.1
  • 31
    • 0030921405 scopus 로고    scopus 로고
    • It was recently reported that the similar reaction can be carried out at 95°C without the reduction the nickel(II) chloride complex: Indolese, A. F. Tetrahedron Lett, 1997, 38, 3513.
    • (1997) Tetrahedron Lett , vol.38 , pp. 3513
    • Indolese, A.F.1
  • 36
    • 33947475845 scopus 로고
    • Kuvilla, H. G.; Nahabedian, K. V. J. Am. Chem. Soc. 1961, 83, 2159, 2164 and 2167. Kuvila, H. G.; Reuwer, J. F.; Mangravite, J. A. J. Am. Chem. Soc. 1964, 86, 2666.
    • (1961) J. Am. Chem. Soc. , vol.83 , pp. 2159
    • Kuvilla, H.G.1    Nahabedian, K.V.2
  • 41
    • 0004190075 scopus 로고
    • Academic: New York
    • For general reviews: (c) Kochi, J. K. Organometallic Mechanisms and Catalysis; Academic: New York, 1978. (d) Hartley, F. R.; Patai, S. The Chemistry of Metal-Carbon Bond; Wiley: New York, 1985; Vol. 3. (e) Hegedus, L. S. Organometallics in Organic Synthesis; Schlosser, M., Ed.; Wiley: New York, 1994; p 383.
    • (1978) Organometallic Mechanisms and Catalysis
    • Kochi, J.K.1
  • 42
    • 84949743662 scopus 로고
    • Wiley: New York
    • For general reviews: (c) Kochi, J. K. Organometallic Mechanisms and Catalysis; Academic: New York, 1978. (d) Hartley, F. R.; Patai, S. The Chemistry of Metal-Carbon Bond; Wiley: New York, 1985; Vol. 3. (e) Hegedus, L. S. Organometallics in Organic Synthesis; Schlosser, M., Ed.; Wiley: New York, 1994; p 383.
    • (1985) The Chemistry of Metal-Carbon Bond , vol.3
    • Hartley, F.R.1    Patai, S.2
  • 43
    • 0006911080 scopus 로고
    • Schlosser, M., Ed.; Wiley: New York
    • For general reviews: (c) Kochi, J. K. Organometallic Mechanisms and Catalysis; Academic: New York, 1978. (d) Hartley, F. R.; Patai, S. The Chemistry of Metal-Carbon Bond; Wiley: New York, 1985; Vol. 3. (e) Hegedus, L. S. Organometallics in Organic Synthesis; Schlosser, M., Ed.; Wiley: New York, 1994; p 383.
    • (1994) Organometallics in Organic Synthesis , pp. 383
    • Hegedus, L.S.1
  • 49
    • 85033154841 scopus 로고    scopus 로고
    • note
    • 18a
  • 56
    • 0742313889 scopus 로고    scopus 로고
    • The oxidative addition of the C-B bond to the palladium(0) complexes has been reported; however, this process has still remained obscure: (a) Moreno-Mañas, M.; Pérez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346-2349. (b) Cho, C. S.; Motofusa, S.; Ohe, K.; Uemura, S. J. Org. Chem. 1995, 60, 883-888.
    • (1996) J. Org. Chem. , vol.61 , pp. 2346-2349
    • Moreno-Mañas, M.1    Pérez, M.2    Pleixats, R.3
  • 57
    • 33751156934 scopus 로고
    • The oxidative addition of the C-B bond to the palladium(0) complexes has been reported; however, this process has still remained obscure: (a) Moreno-Mañas, M.; Pérez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346-2349. (b) Cho, C. S.; Motofusa, S.; Ohe, K.; Uemura, S. J. Org. Chem. 1995, 60, 883-888.
    • (1995) J. Org. Chem. , vol.60 , pp. 883-888
    • Cho, C.S.1    Motofusa, S.2    Ohe, K.3    Uemura, S.4
  • 58
    • 85033131412 scopus 로고    scopus 로고
    • note
    • 36
  • 59
    • 0001322607 scopus 로고
    • Kong, K. C.; Cheng, C.-H. J. Am. Chem. Soc. 1991, 113, 6313-6315. Morita, D. K.; Stille, J. K.; Norton, J. R. Ibid. 1995, 117, 8576-8581.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 6313-6315
    • Kong, K.C.1    Cheng, C.-H.2
  • 64
    • 0343260254 scopus 로고
    • North-Holland: Amsterdam
    • Nesmeyanov, A. N.; Sokolik, R. A. Methods of Elemento-Organic Chemistry; North-Holland: Amsterdam, 1967; Vol. 1. Mikhailov, B. M.; Bubnov, Yu. N. Organoboron Compounds in Organic Synthesis; Harwood Academic Pub.: Amsterdam, 1983.
    • (1967) Methods of Elemento-Organic Chemistry , vol.1
    • Nesmeyanov, A.N.1    Sokolik, R.A.2
  • 65


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