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Volumn 73, Issue 18, 2008, Pages 7376-7379

Palladium-catalyzed reactions of arylindium reagents prepared directly from aryl iodides and indium metal

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CHEMICAL REACTIONS; CHLORINE COMPOUNDS; INDIUM; LITHIUM; METALS; PALLADIUM; TRANSITION METALS;

EID: 52449096682     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801074g     Document Type: Article
Times cited : (55)

References (48)
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    • Recently, a directed ortho-lithiation/transmetalation sequence was used in the preparation of triarylindium reagents. Pena, M. A.; Perez Sestelo, J.; Sarandeses, L. A. J. Org. Chem. 2007, 72, 1271.
    • Recently, a directed ortho-lithiation/transmetalation sequence was used in the preparation of triarylindium reagents. Pena, M. A.; Perez Sestelo, J.; Sarandeses, L. A. J. Org. Chem. 2007, 72, 1271.
  • 22
    • 52449096852 scopus 로고    scopus 로고
    • German Patent DE 102006015378, In the preparation of this manuscript, we became aware of a manuscript in review J. Am. Chem. Soc, by Knochel and Chen detailing the direct insertion of indium into aryl and heteroaryl iodides and the cross-coupling of the so-formed indium reagents with aryl halide to form biaryls
    • Knochel, P.; Gavryushin, A.; Malakhov, V. A. German Patent DE 102006015378, 2007. In the preparation of this manuscript, we became aware of a manuscript in review (J. Am. Chem. Soc.) by Knochel and Chen detailing the direct insertion of indium into aryl and heteroaryl iodides and the cross-coupling of the so-formed indium reagents with aryl halide to form biaryls.
    • (2007)
    • Knochel, P.1    Gavryushin, A.2    Malakhov, V.A.3
  • 25
    • 33751329085 scopus 로고    scopus 로고
    • Knochel, P, Ed, Wiley-VCH: Weinheim, Germany
    • (c) Handbook of Functionalized Organometallics; Knochel, P., Ed.; Wiley-VCH: Weinheim, Germany, 2005; Vol. 1, p 109.
    • (2005) Handbook of Functionalized Organometallics , vol.1 , pp. 109
  • 26
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    • (a) Li, C.-J. Chem. Rev. 1993, 93, 2023.
    • (1993) Chem. Rev , vol.93 , pp. 2023
    • Li, C.-J.1
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    • (g) Li, C.-J. Chem. Rev. 2005, 105, 3095.
    • (2005) Chem. Rev , vol.105 , pp. 3095
    • Li, C.-J.1
  • 33
    • 52449086851 scopus 로고    scopus 로고
    • Indium containing 0.1% Mg was prepared my mixing 102.6 mg of indium metal with 11.4 mg of commercially available indium containing 1% Mg (Aldrich).
    • Indium containing 0.1% Mg was prepared my mixing 102.6 mg of indium metal with 11.4 mg of commercially available indium containing 1% Mg (Aldrich).
  • 34
    • 34547203012 scopus 로고    scopus 로고
    • For a previous preparation of 3a, see: So, C. M.; Lau, C. P.; Kwong, F. Y. Org. Lett. 2008, 9, 2795.
    • For a previous preparation of 3a, see: So, C. M.; Lau, C. P.; Kwong, F. Y. Org. Lett. 2008, 9, 2795.
  • 35
    • 52449120857 scopus 로고    scopus 로고
    • Electron-deficient aryl bromides were also suitable partners for the cross-coupling reaction with the in situ formed arylindium reagents, furnishing biaryl products 3 in similar or slightly lower yields when compared to the corresponding aryl iodides. Electron-rich aryl bromides, however, gave very poor yields 5-20, of cross-coupled products
    • Electron-deficient aryl bromides were also suitable partners for the cross-coupling reaction with the in situ formed arylindium reagents, furnishing biaryl products 3 in similar or slightly lower yields when compared to the corresponding aryl iodides. Electron-rich aryl bromides, however, gave very poor yields (5-20%) of cross-coupled products.
  • 40
    • 52449085167 scopus 로고    scopus 로고
    • While the indium metal recovered after the insertion reaction (30% of the total used) could be directly reused in insertion and cross-coupling reactions with minimal (< 10, decrease in yield, the indium metal recovered after zinc-mediated reduction of the residual aqueous indium salts (50-60% of the total used) was a softball-like clump that could not be reused directly because of its decreased surface area compared to indium powder. Work on preparing this material for reuse in insertion and cross-coupling reactions is currently in progress
    • While the indium metal recovered after the insertion reaction (30% of the total used) could be directly reused in insertion and cross-coupling reactions with minimal (< 10%) decrease in yield, the indium metal recovered after zinc-mediated reduction of the residual aqueous indium salts (50-60% of the total used) was a softball-like clump that could not be reused directly because of its decreased surface area compared to indium powder. Work on preparing this material for reuse in insertion and cross-coupling reactions is currently in progress.
  • 47
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    • Van Rheenen, V.; Cha, D. Y.; Hartley, W. M. Organic Synthesis; Wiley: New York, 1988; Collect. VI, p 342.
    • (b) Van Rheenen, V.; Cha, D. Y.; Hartley, W. M. Organic Synthesis; Wiley: New York, 1988; Collect. Vol. VI, p 342.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.