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Volumn 34, Issue , 2008, Pages 46-57

Metal boryl compounds and metal-catalysed borylation processes: Synthetic applications and mechanistic considerations

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EID: 41749096552     PISSN: 03010074     EISSN: None     Source Type: Book Series    
DOI: 10.1039/b606112p     Document Type: Review
Times cited : (41)

References (124)
  • 1
    • 33747883138 scopus 로고    scopus 로고
    • See, for example: (a) H. Braunschweig, D. Kollann and D. Rais, Angew. Chem. Int. Ed., 2006, 45, 5254;
    • See, for example: (a) H. Braunschweig, D. Kollann and D. Rais, Angew. Chem. Int. Ed., 2006, 45, 5254;
  • 6
    • 18244395541 scopus 로고    scopus 로고
    • For reviews on metal catalysed hydroboration, see: a
    • For reviews on metal catalysed hydroboration, see: (a) A. M. Carroll, T. P. O'Sullivan and P. J. Guiry, Adv. Synth. Catal., 2005, 347, 609;
    • (2005) Adv. Synth. Catal , vol.347 , pp. 609
    • Carroll, A.M.1    O'Sullivan, T.P.2    Guiry, P.J.3
  • 11
    • 33749672147 scopus 로고    scopus 로고
    • For reviews on metal-catalysed diboration, see:, ed. D. E. Kaufmann, Georg Thieme, Stuttgart
    • (f) For reviews on metal-catalysed diboration, see: T. B. Marder, in Product Subclass 3: Diborane(4) Compounds, Science of Synthesis, ed. D. E. Kaufmann, Georg Thieme, Stuttgart, 2005, vol. 6, pp. 117-137;
    • (2005) Product Subclass 3: Diborane(4) Compounds, Science of Synthesis , vol.6 , pp. 117-137
    • Marder, T.B.1
  • 21
    • 41749105186 scopus 로고    scopus 로고
    • AllyChem Co. Ltd, BASF, Boron Molecular Pty, and Frontier Scientific, Inc., are all manufacturing diboron compounds in bulk quantities (currently up to ca. 100 Kg scale in certain cases), and the scale of manufacture is likely to increase. This has also brought about a dramatic lowering of the price of the diboron reagents, which continues to make them more attractive reagents for use in synthesis.
    • AllyChem Co. Ltd, BASF, Boron Molecular Pty, and Frontier Scientific, Inc., are all manufacturing diboron compounds in bulk quantities (currently up to ca. 100 Kg scale in certain cases), and the scale of manufacture is likely to increase. This has also brought about a dramatic lowering of the price of the diboron reagents, which continues to make them more attractive reagents for use in synthesis.
  • 30
    • 41749098451 scopus 로고    scopus 로고
    • For the preparation of more soluble, substituted bis(catecholato)-diboron derivatives, see ref. 6
    • (d) For the preparation of more soluble, substituted bis(catecholato)-diboron derivatives, see ref. 6.
  • 32
    • 33749672745 scopus 로고    scopus 로고
    • See also
    • (b) See also: T. B. Marder, Science, 2006, 314, 69;
    • (2006) Science , vol.314 , pp. 69
    • Marder, T.B.1
  • 36
    • 84978362719 scopus 로고    scopus 로고
    • See, for example: (a) H. W. Wanzlick, Angew. Chem. Int. Ed., 1962, 1, 75;
    • See, for example: (a) H. W. Wanzlick, Angew. Chem. Int. Ed., 1962, 1, 75;
  • 39
    • 0037090932 scopus 로고    scopus 로고
    • W. A. Hermann, Angew. Chem. Im. Ed., 2002, 41, 1290;
    • (d) W. A. Hermann, Angew. Chem. Im. Ed., 2002, 41, 1290;
  • 42
    • 41749088354 scopus 로고    scopus 로고
    • For examples of early reports of nucleophilic boryl-like species, see discussion in references 8a, c
    • For examples of early reports of nucleophilic boryl-like species, see discussion in references 8(a)-(c).
  • 56
    • 0035802156 scopus 로고    scopus 로고
    • 19b H. A. Ali, I. Goldberg and M. Srebnik, Organometallics, 2001, 20, 3962.
    • 19b H. A. Ali, I. Goldberg and M. Srebnik, Organometallics, 2001, 20, 3962.
  • 57
    • 0037170637 scopus 로고    scopus 로고
    • Kabalka et al. reported that 10 mol% Rh(PPh3) 3Cl catalysed the addition of B2pin2 and B 2neop2 to α,β-unsaturated carbonyl compounds in toluene at 80°C in 10-14 h but we have had difficulty reproducing findings in this paper. G. W. Kabalka, B. C. Das and S. Das, Tetrahedron Lett, 2002, 43, 2323
    • 2 to α,β-unsaturated carbonyl compounds in toluene at 80°C in 10-14 h but we have had difficulty reproducing findings in this paper. G. W. Kabalka, B. C. Das and S. Das, Tetrahedron Lett., 2002, 43, 2323.
  • 69
    • 19744378397 scopus 로고    scopus 로고
    • For a study of the Rh-catalysed diboration of imines, see
    • (c) For a study of the Rh-catalysed diboration of imines, see: T. M. Cameron, R. T. Baker and S. A. Westcott, Chem. Commun., 1998, 2395.
    • (1998) Chem. Commun , pp. 2395
    • Cameron, T.M.1    Baker, R.T.2    Westcott, S.A.3
  • 70
    • 41749103226 scopus 로고    scopus 로고
    • 26 will be reported in due course: H. Zhao, L. Dang, Z. Lin and T. B. Marder, manuscript in preparation.
    • 26 will be reported in due course: H. Zhao, L. Dang, Z. Lin and T. B. Marder, manuscript in preparation.
  • 78
    • 27644451916 scopus 로고    scopus 로고
    • For examples of the related β-silyl elimination process, see: B. Marciniec, Coord. Chem. Rev, 2005, 249, 2374
    • (b) For examples of the related β-silyl elimination process, see: B. Marciniec, Coord. Chem. Rev., 2005, 249, 2374.
  • 79
    • 0038034652 scopus 로고    scopus 로고
    • For studies of alkene metathesis using vinylboronates, see: a
    • For studies of alkene metathesis using vinylboronates, see: (a) C. Morrill and R. H. Grubbs, J. Org. Chem., 2003, 68, 6031;
    • (2003) J. Org. Chem , vol.68 , pp. 6031
    • Morrill, C.1    Grubbs, R.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.