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Volumn 39, Issue 43, 2010, Pages 10391-10400

Pd-catalysed regioselective C-H functionalisation of 2-pyrones

Author keywords

[No Author keywords available]

Indexed keywords

AMBIENT TEMPERATURES; CATIONIC PALLADIUM; FUNCTIONALISATION; PHOSPHONIUM SALTS; REACTION MECHANISM; REGIO-SELECTIVE; RELATED COMPOUNDS; SYNTHETIC METHODOLOGY;

EID: 78049335905     PISSN: 14779226     EISSN: 14779234     Source Type: Journal    
DOI: 10.1039/c0dt00421a     Document Type: Conference Paper
Times cited : (24)

References (80)
  • 4
    • 0003049435 scopus 로고    scopus 로고
    • Recent advances in Diels-Alder cycloadditions of 2-pyrones
    • JAI Press, Greenwich
    • B. T. Woodard and G. H. Posner, Recent advances in Diels-Alder cycloadditions of 2-pyrones, in Advances in Cycloaddition, JAI Press, Greenwich, 1999, Vol. 5, p. 47.
    • (1999) Advances in Cycloaddition , vol.5 , pp. 47
    • Woodard, B.T.1    Posner, G.H.2
  • 29
    • 34250323132 scopus 로고    scopus 로고
    • and references cited therein
    • For other innovative syntheses, see I.-J. Shin E. S. Choi C. G. Cho Angew. Chem., Int. Ed. 2007 46 2303 2305 and references cited therein
    • (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 2303-2305
    • Shin, I.-J.1    Choi, E.S.2    Cho, C.G.3
  • 34
    • 77949568995 scopus 로고    scopus 로고
    • Recently, this precatalyst was found to highly effective for the benzylation of N-Boc indole boronic acids. see A. M. Kearney A. Landry-Bayle L. Gomez Tetrahedron Lett. 2010 51 2281 2283
    • (2010) Tetrahedron Lett. , vol.51 , pp. 2281-2283
    • Kearney, A.M.1    Landry-Bayle, A.2    Gomez, L.3
  • 41
    • 78049334066 scopus 로고    scopus 로고
    • Ph.D. Thesis, MMU, Manchester, UK
    • L. R. Marrison, Ph.D. Thesis, MMU, Manchester, UK, 1998
    • (1998)
    • Marrison, L.R.1
  • 42
    • 78049352280 scopus 로고    scopus 로고
    • 1H NMR spectroscopic analysis of the crude reaction mixtures
    • 1H NMR spectroscopic analysis of the crude reaction mixtures.
  • 43
    • 0006549126 scopus 로고
    • ed J. B. Harborne, T. J. Mabry and H. Mabry ed., Chapman and Hall, London The synthesis of this compound has attracted much attention, most recently 9985-9989
    • In The Flavanoids, J. B. Harborne, T. J. Mabry, and, H. Mabry, ed., 1975, Chapman and Hall, London
    • (1975) The Flavanoids
  • 44
    • 28044442286 scopus 로고    scopus 로고
    • The synthesis of this compound has attracted much attention, most recently T. Yao, D. Yue, R. C. Larock, J. Org. Chem., 2005, 70, 9985-9989
    • (2005) J. Org. Chem. , vol.70 , pp. 9985-9989
    • Yao, T.1    Yue, D.2    Larock, R.C.3
  • 46
    • 78049346853 scopus 로고    scopus 로고
    • 2] where C* is any carbon-based group bonded directly to Pd
    • 2] where C* is any carbon-based group bonded directly to Pd.
  • 49
    • 33644919911 scopus 로고    scopus 로고
    • Structure A - I-Pd-C 168.30°; P-Pd-P 174.02°, Structure B I-Pd-C176.50°;P-Pd-P172.39°,see: D. Taher B. Walfort H. Lang Inorg. Chim. Acta 2006 359 1899 1906
    • (2006) Inorg. Chim. Acta , vol.359 , pp. 1899-1906
    • Taher, D.1    Walfort, B.2    Lang, H.3
  • 50
    • 33846077486 scopus 로고    scopus 로고
    • Representative papers detailing "CC" Pd-π interactions, see: D. B. G. Williams M. L. Shaw Tetrahedron 2007 63 1624 1629
    • (2007) Tetrahedron , vol.63 , pp. 1624-1629
    • Williams, D.B.G.1    Shaw, M.L.2
  • 63
    • 84879868832 scopus 로고    scopus 로고
    • Ed., M. Oestreich, John Wiley & Sons, Hoboken, ISBN 978-0470033944
    • In The Mizoroki-Heck Reaction, Ed., M. Oestreich, John Wiley & Sons, Hoboken, 2009, ISBN 978-0470033944
    • (2009) The Mizoroki-Heck Reaction
  • 64
    • 31944442069 scopus 로고    scopus 로고
    • Some caution is necessary here as it has been reported that an intermolecular base-assisted deprotonation can take place (in the presence of bidentate phosphine ligands), see ref. 25b. For monodentate ligands, it was not possible to distinguish between inter- and intra-molecular base-assisted deprotonation reactions. Relevant references: D. García-Cuadrado A. A. C. Braga F. Maseras A. M. Echavarren J. Am. Chem. Soc. 2006 128 1066 1067
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 1066-1067
    • García-Cuadrado, D.1    Braga, A.A.C.2    Maseras, F.3    Echavarren, A.M.4
  • 69
    • 31544455027 scopus 로고    scopus 로고
    • Also see ref. 30 and 31
    • However, it is unlikely that anti-β-hydrogen elimination occurs (in the absence of syn-β-hydrogens) L.-C. Campeau M. Parisien A. Jean K. Fagnou J. Am. Chem. Soc. 2006 128 581 590
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 581-590
    • Campeau, L.-C.1    Parisien, M.2    Jean, A.3    Fagnou, K.4
  • 73
    • 33846918696 scopus 로고    scopus 로고
    • For a general review on direct arylation mechanisms and synthetic applications see D. Alberico M. E. Scott M. Lautens Chem. Rev. 2007 107 174 238
    • (2007) Chem. Rev. , vol.107 , pp. 174-238
    • Alberico, D.1    Scott, M.E.2    Lautens, M.3
  • 74
    • 78049349445 scopus 로고    scopus 로고
    • DMA and DMF are commonly used solvents for direct arylation, see references 6a, 25a,b, and those references cited therein
    • DMA and DMF are commonly used solvents for direct arylation, see references 6a, 25a,b, and those references cited therein.
  • 75
    • 78049344315 scopus 로고    scopus 로고
    • 2O without significantly perturbing the H/D balance
    • 2O without significantly perturbing the H/D balance.
  • 76
    • 78049341727 scopus 로고    scopus 로고
    • During the submission of this paper, we ran two reactions of 5a→ 6a where THF was replaced by DMF under otherwise identical conditions to those given in entry 8, Table 1. In both cases, no product formation was observed
    • During the submission of this paper, we ran two reactions of 5a→ 6a where THF was replaced by DMF under otherwise identical conditions to those given in entry 8, Table 1. In both cases, no product formation was observed.
  • 77
    • 67649378424 scopus 로고    scopus 로고
    • During the final preparative stages of this manuscript we found a report on a 'Heck-like' reaction of a coumarin containing a tethered aromatic bromide. Whilst the reaction requires a higher temperature (100 °C) and unique Pd precatalyst containing a 1,2-cyclobutadiene-substituted CpCoCb diphosphine ligand, it operates in dioxane solvent with DABCO as the base, see: C.-P. Chang S. V. Pradiuldi F.-E. Hong Inorg. Chem. Commun. 2009 12 596 598 No further mechanistic details were provided in this paper (vis-à-vis CMD (AMLA-6) versus Heck-like reaction pathways).
    • (2009) Inorg. Chem. Commun. , vol.12 , pp. 596-598
    • Chang, C.-P.1    Pradiuldi, S.V.2    Hong, F.-E.3
  • 79
    • 78049343301 scopus 로고    scopus 로고
    • Bruker AXS GmbH, Karlsruhe, Germany
    • Saint+ (v6.22) Bruker AXS, Bruker AXS GmbH, Karlsruhe, Germany
    • Saint+ (v6.22) Bruker AXS


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