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Volumn 1, Issue 8, 1999, Pages 1183-1186

N-cumyl benzamide, sulfonamide, and aryl O-carbamate directed metalation groups. Mild hydrolytic lability for facile manipulation of directed ortho metalation derived aromatics

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EID: 0001491460     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990846b     Document Type: Article
Times cited : (83)

References (48)
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    • Substrate 1h is compromised, to various degrees, by the requirement of low-temperature (-90 °C) metalation conditions, ketone byproduct formation, and less effective DMG power compared to the amides
    • (b) Moyroud, J.; Guesnet, J.; Bennetau, B.; Mortier, J. Tetrahedron Lett. 1995, 36, 881. Substrate 1h is compromised, to various degrees, by the requirement of low-temperature (-90 °C) metalation conditions, ketone byproduct formation, and less effective DMG power compared to the amides.
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    • (1998) J. Org. Chem. , vol.63 , pp. 2054
    • Caron, S.1    Hawkins, J.M.2
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    • 2O from 0°C to room temperature (18 h, 95% yield) instead of Raney nickel. 1,1-Diphenylethylamine was similarly prepared
    • 2O from 0°C to room temperature (18 h, 95% yield) instead of Raney nickel. 1,1-Diphenylethylamine was similarly prepared.
    • (1978) Synthesis , pp. 24
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    • and references therein. For solid support reactions, see
    • (a) James, C. A.; Snieckus, V. Tetrahedron Lett. 1997, 38, 8149 and references therein. For solid support reactions, see:
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8149
    • James, C.A.1    Snieckus, V.2
  • 19
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    • and references therein
    • Previous non-DoM routes involve nucleophilic aromatic substitution of 3-nitrophthalimide, made via nitration of phthalic acid; see: Fischer, W. Helv. Chim. Acta 1991, 74, 1119 and references therein.
    • (1991) Helv. Chim. Acta , vol.74 , pp. 1119
    • Fischer, W.1
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    • note
    • 26NOSi 312.1784, found 312.1780.
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    • 0042089026 scopus 로고    scopus 로고
    • submitted for publication
    • The product corresponds to a penultimate intermediate for a high-volume commercial product, OTBN (o-tolylbenzonitrile) from Clariant; see: Haber, S.; Koch, M. Innovations Pharm. Technol., submitted for publication.
    • Innovations Pharm. Technol.
    • Haber, S.1    Koch, M.2
  • 34
    • 0041587871 scopus 로고    scopus 로고
    • Confirmation of C-3 substituted products was secured by parallel HMQC and HMBC 2-D NMR experiments of deuterated products
    • Confirmation of C-3 substituted products was secured by parallel HMQC and HMBC 2-D NMR experiments of deuterated products.
  • 38
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    • German Patent 2 200 115, 1973
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    • Schefczik, E.1
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    • (b) Schefczik, E. German Patent 2 200 115, 1973; Chem. Abstr. 1974, 80, 4909c.
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    • German Patent 2 511 092, 1975
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    • German Patent 2 744 137, 1978
    • Prepared according to: Takematsu, T.; Konnai, M.; Omokawa, H. German Patent 2 744 137, 1978; Chem. Abstr. 1978, 89, 42793d.
    • Takematsu, T.1    Konnai, M.2    Omokawa, H.3
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  • 48
    • 0041587870 scopus 로고    scopus 로고
    • Manuscript in preparation
    • We have recently demonstrated that the N-cumyl amide DMG is also effective in ferrocene DoM chemistry: Metallinos. C.; Bessler, C.; Green, L.; Snieckus, V. Manuscript in preparation.
    • Metallinos, C.1    Bessler, C.2    Green, L.3    Snieckus, V.4


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