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Volumn 62, Issue 2, 1997, Pages 261-274

Nickel- and Palladium-Catalyzed Homocoupling of Aryl Triflates. Scope, Limitation, and Mechanistic Aspects

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EID: 0001306851     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961464b     Document Type: Article
Times cited : (139)

References (123)
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    • For reviews on the synthesis of biaryls see ref 1 and: (a) Fanta, P. E. Synthesis 1974, 9.
    • (1974) Synthesis , pp. 9
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    • note
    • 3, which makes the workup more complicated.
  • 71
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    • 2-catalyzed polymerization of aryl bis- (triflates) was also reported. See: Persec, V.; Okita, S.; Weiss, R. Macromolecules 1992, 25, 1816.
    • (1992) Macromolecules , vol.25 , pp. 1816
    • Persec, V.1    Okita, S.2    Weiss, R.3
  • 73
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    • To our knowledge the electrochemical reduction of aryl triflates is not reported. The electrochemical reduction of aryl tosylates affords mainly phenols. See: Civitello, E. R.; Rapoport, H. J. Org. Chem. 1992, 57, 834.
    • (1992) J. Org. Chem. , vol.57 , pp. 834
    • Civitello, E.R.1    Rapoport, H.2
  • 77
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    • For the determination of rate constants by cyclic voltammetry see ref 22
    • For the determination of rate constants by cyclic voltammetry see ref 22.
  • 78
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    • 15
    • 15
  • 80
    • 0040121540 scopus 로고
    • The palladium-catalyzed electroreduction of aryl triflates to arenes, in the presence of a proton source, has been recently reported. See: Chiarotto, I.; Cacchi, S.; Pace, P.; Carelli, I. J. Electroanal. Chem. 1995, 385, 235.
    • (1995) J. Electroanal. Chem. , vol.385 , pp. 235
    • Chiarotto, I.1    Cacchi, S.2    Pace, P.3    Carelli, I.4
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    • note
    • 13d
  • 97
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    • note
    • 2, although formally an 18e complex, is still able to catalyze Heck reaction. See ref 31d.
  • 98
    • 85033155068 scopus 로고    scopus 로고
    • 2, although formally an 18e complex, is still able to catalyze Heck reaction. See ref 31d
    • 2, although formally an 18e complex, is still able to catalyze Heck reaction. See ref 31d.
  • 99
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    • 18a,b
    • 18a,b
  • 101
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    • Racemic diphosphines in the biphenyls series were synthesized from aryl iodides by an Ullmann reaction in the presence of a stoechiometric amount of copper(0). See: Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Helv. Chim. Acta 1991, 74, 370.
    • (1991) Helv. Chim. Acta , vol.74 , pp. 370
    • Schmid, R.1    Foricher, J.2    Cereghetti, M.3    Schönholzer, P.4
  • 103
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    • For the reduction of phosphine oxide to the corresponding phosphine see: (a) Naumann, K.; Zon, G.; Mislow, K. J. Am. Chem. Soc. 1969, 91, 7012. (b) Uozomi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 7012
    • Naumann, K.1    Zon, G.2    Mislow, K.3
  • 104
    • 0001514035 scopus 로고
    • For the reduction of phosphine oxide to the corresponding phosphine see: (a) Naumann, K.; Zon, G.; Mislow, K. J. Am. Chem. Soc. 1969, 91, 7012. (b) Uozomi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945.
    • (1993) J. Org. Chem. , vol.58 , pp. 1945
    • Uozomi, Y.1    Tanahashi, A.2    Lee, S.-Y.3    Hayashi, T.4
  • 105
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    • Indeed, we observed from Table 6 that using two bidentate phosphine ligands per palladium resulted in either a nonreactive catalyst (entry 7) or a less efficient one (entry 11)
    • Indeed, we observed from Table 6 that using two bidentate phosphine ligands per palladium resulted in either a nonreactive catalyst (entry 7) or a less efficient one (entry 11).
  • 116
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    • The spectra were compared to those of a commercial sample
    • The spectra were compared to those of a commercial sample.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.