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Volumn 30, Issue 6, 2011, Pages 1299-1302

Nickel-catalyzed cross-coupling of organogold reagents

Author keywords

[No Author keywords available]

Indexed keywords

CROSS COUPLING REACTIONS; CROSS-COUPLINGS; ELECTRON-RICH; HIGH YIELD; NICKEL CATALYSIS; ORGANOGOLD COMPOUNDS; VINYL BROMIDES;

EID: 79952983010     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200060x     Document Type: Article
Times cited : (40)

References (57)
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    • For an early example of a palladium-catalyzed reaction that could proceed through an organogold intermediate, see
    • For an early example of a palladium-catalyzed reaction that could proceed through an organogold intermediate, see: Jones, L. A.; Sanz, S.; Laguna, M. Catal. Today 2006, 122, 303
    • (2006) Catal. Today , vol.122 , pp. 303
    • Jones, L.A.1    Sanz, S.2    Laguna, M.3
  • 23
  • 24
    • 79952927036 scopus 로고    scopus 로고
    • In contrast to eq 3, no gold mirror was observed in the course of these reactions
    • In contrast to eq 3, no gold mirror was observed in the course of these reactions.
  • 25
    • 84965578199 scopus 로고
    • Standard reduction potential of Au(I):;;, Eds.; CRC: Boca Raton,; Vol., pp D-
    • Standard reduction potential of Au(I): CRC Handbook of Chemisty and Physics; Weast, R. C.; Astle, M. J., Eds.; CRC: Boca Raton, 1980; Vol. 60, pp D- 155.
    • (1980) CRC Handbook of Chemisty and Physics , vol.60 , pp. 155
    • Weast, R.C.1    Astle, M.J.2
  • 26
    • 0037847929 scopus 로고
    • The one-electron oxidation potentials of many nickel complexes have been investigated. For one example, see
    • The one-electron oxidation potentials of many nickel complexes have been investigated. For one example, see: Louati, A.; Huhn, M. Inorg. Chem. 1993, 32, 3601
    • (1993) Inorg. Chem. , vol.32 , pp. 3601
    • Louati, A.1    Huhn, M.2
  • 27
    • 0030921405 scopus 로고    scopus 로고
    • For representative examples of nickel-catalyzed cross-coupling reactions that are analogous to palladium-catalyzed processes, see
    • For representative examples of nickel-catalyzed cross-coupling reactions that are analogous to palladium-catalyzed processes, see: Indolese, A. F. Tetrahedron Lett. 1997, 38, 3513
    • (1997) Tetrahedron Lett. , vol.38 , pp. 3513
    • Indolese, A.F.1
  • 31
    • 55549084571 scopus 로고    scopus 로고
    • For some recent examples of catalytic reactions accessible uniquely to nickel, see
    • For some recent examples of catalytic reactions accessible uniquely to nickel, see: Quasdorf, K. W.; Tian, X.; Garg, N. K. J. Am. Chem. Soc. 2008, 130, 14422
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 14422
    • Quasdorf, K.W.1    Tian, X.2    Garg, N.K.3
  • 35
    • 79952921172 scopus 로고    scopus 로고
    • An initial screen of cross-coupling conditions with 4-halobenzaldehydes and 4a revealed comparable reactivity between aryl bromides and aryl iodides. Bromides were selected for this study due to their ready availability when compared to the corresponding iodide. The coupling of 4-chlorobenzaldehyde proceeded with diminished yield (20% after 6 h at 25 °C)
    • An initial screen of cross-coupling conditions with 4-halobenzaldehydes and 4a revealed comparable reactivity between aryl bromides and aryl iodides. Bromides were selected for this study due to their ready availability when compared to the corresponding iodide. The coupling of 4-chlorobenzaldehyde proceeded with diminished yield (20% after 6 h at 25 °C).
  • 42
    • 0000631827 scopus 로고    scopus 로고
    • For some examples of the formation of carbon radicals by nickel catalysts, see
    • For some examples of the formation of carbon radicals by nickel catalysts, see: Vaupel, A.; Knochel, P. J. Org. Chem. 1996, 61, 5743
    • (1996) J. Org. Chem. , vol.61 , pp. 5743
    • Vaupel, A.1    Knochel, P.2
  • 52
    • 79952973067 scopus 로고    scopus 로고
    • With the electron-rich bromide 4-bromotoluene as a cross-coupling partner, organogold compound 4a was a potent enough oxidant to oxidize Ni. The formation of gold mirror was observed in this reaction
    • With the electron-rich bromide 4-bromotoluene as a cross-coupling partner, organogold compound 4a was a potent enough oxidant to oxidize Ni. The formation of gold mirror was observed in this reaction.
  • 53
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    • Concomitant formation of gold mirror occurred
    • Concomitant formation of gold mirror occurred.
  • 56
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    • The combined chemistry of nickel and gold Werner complexes has been investigated. See
    • The combined chemistry of nickel and gold Werner complexes has been investigated. See: Kim, H. P.; Fanwick, P. E.; Kubiak, C. P. J. Organomet. Chem. 1988, 346, C39
    • (1988) J. Organomet. Chem. , vol.346 , pp. 39
    • Kim, H.P.1    Fanwick, P.E.2    Kubiak, C.P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.