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Volumn 24, Issue 2, 2005, Pages 245-255

Rhenium-containing phosphorus donor ligands for palladium-catalyzed suzuki cross-coupling reactions: A new strategy for high-activity systems

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CHROMATOGRAPHIC ANALYSIS; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; ELECTRONIC PROPERTIES; HYDROGENATION; ORGANIC ACIDS; ORGANIC SOLVENTS; RHENIUM COMPOUNDS; SPECTROSCOPIC ANALYSIS;

EID: 12844288928     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0492956     Document Type: Article
Times cited : (38)

References (74)
  • 6
    • 3242659154 scopus 로고    scopus 로고
    • (e) Miura, M. Angew. Chem., Int. Ed. 2004, 43, 2201; Angew. Chem. 2004, 116, 2251.
    • (2004) Angew. Chem. , vol.116 , pp. 2251
  • 9
    • 3042654141 scopus 로고    scopus 로고
    • (b) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871; Angew. Chem. 2004, 116, 1907.
    • (2004) Angew. Chem. , vol.116 , pp. 1907
  • 12
    • 0034680642 scopus 로고    scopus 로고
    • This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 4153
    • Zapf, A.1    Ehrentraut, A.2    Beller, M.3
  • 13
    • 0001211425 scopus 로고    scopus 로고
    • This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
    • (2000) Angew. Chem. , vol.112 , pp. 4315
  • 14
    • 12844273996 scopus 로고    scopus 로고
    • This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
    • (2001) J. Chem. Soc., Dalton Trans. , vol.2721
    • Clarke, M.L.1    Cole-Hamilton, D.J.2    Woolins, J.D.3
  • 15
    • 0037204954 scopus 로고    scopus 로고
    • and earlier work cited therein
    • This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
    • (2002) J. Org. Chem. , vol.67 , pp. 3643
    • Li, G.Y.1
  • 16
    • 0037047555 scopus 로고    scopus 로고
    • This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
    • (2002) J. Org. Chem. , vol.67 , pp. 5553
    • Kataoka, N.1    Shelby, Q.2    Stambuli, J.P.3    Hartwig, J.F.4
  • 17
    • 2942700302 scopus 로고    scopus 로고
    • This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
    • (2004) Aldrichim. Acta , vol.37 , pp. 3
    • Verkade, J.G.1    Kisanga, P.B.2
  • 18
    • 1642580702 scopus 로고    scopus 로고
    • This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
    • (2004) Chem. Commun. , pp. 38
    • Zapf, A.1    Jackstell, R.2    Rataboul, F.3    Riermeier, T.4    Monsees, A.5    Fuhrmann, C.6    Shaikh, N.7    Dingerdissen, U.8    Beller, M.9
  • 19
    • 2942518465 scopus 로고    scopus 로고
    • This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 5283
    • Khanapure, S.P.1    Garvey, D.S.2
  • 20
    • 1842733481 scopus 로고    scopus 로고
    • This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
    • (2004) Chem. Eur. J. , vol.10 , pp. 1789
    • An Der Heiden, M.1    Plenio, H.2
  • 41
    • 12844271472 scopus 로고    scopus 로고
    • note
    • To help consolidate a fragmented literature, updated syntheses and characterization of the previously reported rhenium complexes in Scheme 1 (and alternative salts for some cations) are provided in the Supporting Information.
  • 49
    • 0037112673 scopus 로고    scopus 로고
    • Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176; Angew. Chem. 2002, 114, 4350.
    • (2002) Angew. Chem. , vol.114 , pp. 4350
  • 58
    • 4544335033 scopus 로고    scopus 로고
    • (d) Willis, M. C.; Powell, L. H. W.; Claverie, C. K.; Watson, S. J. Angew. Chem., Int. Ed. 2004, 43, 1249; Angew. Chem. 2004, 116, 1269.
    • (2004) Angew. Chem. , vol.116 , pp. 1269
  • 63
    • 12844284222 scopus 로고    scopus 로고
    • note
    • 7,18a
  • 65
    • 12844280214 scopus 로고    scopus 로고
    • note
    • 3 and PPhPh' signals were not observed.
  • 66
    • 85050935423 scopus 로고
    • 2H is pyrophoric and was stored at -32°C in a glovebox. Preparation: (a) Parshall, G. W. Inorg. Synth. 1968, 11, 157. (b) King, R. B.; Cloyd, J. C., Jr. J. Am. Chem. Soc. 1975, 97, 46.
    • (1968) Inorg. Synth. , vol.11 , pp. 157
    • Parshall, G.W.1
  • 67
    • 0007401571 scopus 로고
    • 2H is pyrophoric and was stored at -32°C in a glovebox. Preparation: (a) Parshall, G. W. Inorg. Synth. 1968, 11, 157. (b) King, R. B.; Cloyd, J. C., Jr. J. Am. Chem. Soc. 1975, 97, 46.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 46
    • King, R.B.1    Cloyd Jr., J.C.2
  • 68
    • 12844254678 scopus 로고    scopus 로고
    • note
    • 18a
  • 69
    • 12844285346 scopus 로고    scopus 로고
    • Tentative assignment
    • Tentative assignment
  • 72
    • 0031059866 scopus 로고    scopus 로고
    • Macromolecular Crystallography, Part A
    • (b) "Scalepack" data processing software: Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276 (Macromolecular Crystallography, Part A), 307.
    • (1997) Methods Enzymol. , vol.276 , pp. 307
    • Otwinowski, Z.1    Minor, W.2
  • 73
    • 0004150157 scopus 로고    scopus 로고
    • Program for refinement of crystal structures; University of Göttingen
    • Sheldrick, G. M. SHELX-97, Program for refinement of crystal structures; University of Göttingen, 1997.
    • (1997) SHELX-97
    • Sheldrick, G.M.1


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