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Volumn 43, Issue 39, 2002, Pages 6987-6990

Cyclopropylboronic acid: Synthesis and Suzuki cross-coupling reactions

Author keywords

Cyclopropylboronic acid; Pharmaceutically active molecules; Suzuki cross coupling

Indexed keywords

BROMINE DERIVATIVE; CYCLOPROPANE DERIVATIVE; CYCLOPROPYLBORONIC ACID; UNCLASSIFIED DRUG;

EID: 0037163328     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01606-4     Document Type: Article
Times cited : (79)

References (39)
  • 2
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    • For example, see: (a) Todo, Y.; Takagi, H.; Iino, F.; Fukuorka, Y.; Ikeda, Y.; Tanaka, K.; Saikawa, I.; Narita, H. Chem. Pharm. Bull. 1994, 42, 2049; (b) Turner, W. R.; Suto, M. J. Tetrahedron Lett. 1993, 34, 281.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 281
    • Turner, W.R.1    Suto, M.J.2
  • 7
    • 0030925728 scopus 로고    scopus 로고
    • See, inter alia: (a) Gunnoe, T. B.; White, P. S.; Casarrubios, L.; Templetone, J. L. J. Am. Chem. Soc. 1997, 119, 3171; (b) Du, H.; Yang, F.; Hossain, M. M. Synth. Commun. 1996, 26, 1371; (c) Kawabat, N.; Naka, M.; Yamashita, S. J. Am. Chem. Soc. 1976, 98, 2676.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 3171
    • Gunnoe, T.B.1    White, P.S.2    Casarrubios, L.3    Templetone, J.L.4
  • 8
    • 0029959009 scopus 로고    scopus 로고
    • See, inter alia: (a) Gunnoe, T. B.; White, P. S.; Casarrubios, L.; Templetone, J. L. J. Am. Chem. Soc. 1997, 119, 3171; (b) Du, H.; Yang, F.; Hossain, M. M. Synth. Commun. 1996, 26, 1371; (c) Kawabat, N.; Naka, M.; Yamashita, S. J. Am. Chem. Soc. 1976, 98, 2676.
    • (1996) Synth. Commun. , vol.26 , pp. 1371
    • Du, H.1    Yang, F.2    Hossain, M.M.3
  • 9
    • 0001508441 scopus 로고
    • See, inter alia: (a) Gunnoe, T. B.; White, P. S.; Casarrubios, L.; Templetone, J. L. J. Am. Chem. Soc. 1997, 119, 3171; (b) Du, H.; Yang, F.; Hossain, M. M. Synth. Commun. 1996, 26, 1371; (c) Kawabat, N.; Naka, M.; Yamashita, S. J. Am. Chem. Soc. 1976, 98, 2676.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 2676
    • Kawabat, N.1    Naka, M.2    Yamashita, S.3
  • 17
    • 0000581709 scopus 로고
    • For the use of substituted cyclopropyl(tri-n-butyl)stannanes in coupling reactions, see: (a) Corey, E. J.; Eckrich, T. M. Tetrahedron Lett. 1984, 25, 2415; (b) Piers, E.; Jean, M.; Marrs, P. S. Tetrahedron Lett. 1987, 28, 5075.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 2415
    • Corey, E.J.1    Eckrich, T.M.2
  • 18
    • 0001237355 scopus 로고
    • For the use of substituted cyclopropyl(tri-n-butyl)stannanes in coupling reactions, see: (a) Corey, E. J.; Eckrich, T. M. Tetrahedron Lett. 1984, 25, 2415; (b) Piers, E.; Jean, M.; Marrs, P. S. Tetrahedron Lett. 1987, 28, 5075.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 5075
    • Piers, E.1    Jean, M.2    Marrs, P.S.3
  • 19
    • 0346786657 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147; (b) Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4544.
    • (1999) J. Organomet. Chem. , vol.576 , pp. 147
    • Suzuki, A.1
  • 28
    • 0005123992 scopus 로고    scopus 로고
    • note
    • A report exists claiming cyclopropylboronic acid cannot be made, see: Ref. 6a
  • 29
    • 0005123550 scopus 로고    scopus 로고
    • note
    • Since completion of this work the use of cyclopropylboronic acid for a single cross-coupling reaction has appeared in the patent literature. The boronic acid was not isolated and no yields or data were given. See: Stolle, A.; Dumas, J. P.; Carley, W.; Coish, P. D. G.; Magnuson, S. R.; Wang, Y.; Nagarathnam, D.; Lowe, D. B.; Su, N.; Bullock, W. H.; Campbell, A.-M.; Qi, N.; Baryza, J. L.; Cook, J. H. Substituted indoles, pharmaceutical compositions containg such indoles and their use as PPAR-γ binding agents. International patent WO 2002030895, April 18, 2002.
  • 30
    • 0005123993 scopus 로고    scopus 로고
    • note
    • 3OD): δ 34.3.
  • 31
    • 0005123764 scopus 로고    scopus 로고
    • New compounds gave satisfactory NMR, IR and HRMS or microanalytical data.
    • New compounds gave satisfactory NMR, IR and HRMS or microanalytical data.
  • 32
    • 0005120742 scopus 로고    scopus 로고
    • note
    • 3: C, 72.39; H, 6.94. Found: C, 72.11; H, 6.75%.
  • 33
    • 0005123765 scopus 로고    scopus 로고
    • 2-Bromopyridine gave a 50% yield of bipyridine. The reaction with 3-bromopyridine was complete by LC analysis, but product volatility resulted in a reduced isolated yield.
    • 2-Bromopyridine gave a 50% yield of bipyridine. The reaction with 3-bromopyridine was complete by LC analysis, but product volatility resulted in a reduced isolated yield.
  • 36
    • 0005172926 scopus 로고    scopus 로고
    • Reactions were run with 2-(di-tert-butylphosphino)biphenyl (10 mol%), palladium acetate (5 mol%), potassium fluoride (3 equiv.) in THF at 45°C.
    • Reactions were run with 2-(di-tert-butylphosphino)biphenyl (10 mol%), palladium acetate (5 mol%), potassium fluoride (3 equiv.) in THF at 45°C.


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