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Volumn 62, Issue 27, 2006, Pages 6526-6535

Organolithiums by reductive lithiation: the catalytic aromatic method versus the use of preformed aromatic radical-anions. Naphthalene can behave as a catalyst or an inhibitor

Author keywords

Aromatic catalysis; Dianions; Organolithium; Radical anions; Reductive lithiation

Indexed keywords

ANION; AROMATIC COMPOUND; NAPHTHALENE; ORGANOLITHIUM COMPOUND; RADICAL;

EID: 33646944179     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.03.056     Document Type: Article
Times cited : (26)

References (108)
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    • note
    • Taken in part from the Ph.D. thesis of Mary Dosch Doubleday, University of Pittsburgh, 1991.
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    • note
    • The superior versatility of compounds containing the phenylthio group as substrates for reductive lithiation arises from their almost unique ease of construction, particularly by methods involving C-C bond formation but also by the ability of the phenylthio group to enter a molecule as a nucleophile, electrophile, or radical. In addition, the substrates are almost always able to withstand the powerful nucleophiles/bases that are present in the reductive lithiation conditions. For example, alkyl halides, sulfates, sulfonates, etc. are subject to ready nucleophilic substitution, but most seriously to base induced elimination, thus limiting their use largely to the preparation of primary alkyllithiums unless an aryl or vinyl group is present to increase the rate of the reductive lithiation and favor it over competing processes.
  • 63
    • 33646912065 scopus 로고    scopus 로고
    • Various aryl-substituted N,N-dimethylanilines also decompose to aryllithiums but at far higher temperatures.
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    • Reviews:
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    • Rappoport Z., and Marek I. (Eds), Wiley, Chichester, UK Chapter 11
    • Yus M. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organolithium Compounds (2004), Wiley, Chichester, UK Chapter 11
    • (2004) The Chemistry of Organolithium Compounds
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    • Some more recent papers:
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    • At least one other group has mentioned this assertion in explanation of their use of the CA method:
    • At least one other group has mentioned this assertion in explanation of their use of the CA method:. Manteca I., Etxarri B., Ardeo A., Arrasate S., Osante I., Sotomayor N., and Lete E. Tetrahedron 54 (1998) 12361-12378
    • (1998) Tetrahedron , vol.54 , pp. 12361-12378
    • Manteca, I.1    Etxarri, B.2    Ardeo, A.3    Arrasate, S.4    Osante, I.5    Sotomayor, N.6    Lete, E.7
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    • It is known that alkyllithiums such as 12 tend to exist at equilibrium in the cis configuration.
    • It is known that alkyllithiums such as 12 tend to exist at equilibrium in the cis configuration. Evans D.A., Andrews G.C., and Buckwalter B. J. Am. Chem. Soc. 96 (1974) 5560-5561
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 5560-5561
    • Evans, D.A.1    Andrews, G.C.2    Buckwalter, B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.