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Volumn 76, Issue 1, 2011, Pages 25-34

Iron-catalyzed oxidative coupling of alkylamides with arenes through oxidation of alkylamides followed by Friedel-Crafts alkylation

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC ACTIVITY; CATALYTIC AMOUNTS; CATALYTIC CYCLES; EFFICIENT CATALYSTS; FRIEDEL-CRAFTS ALKYLATION; LEWIS ACID; NUCLEOPHILICITIES; OXIDATIVE COUPLINGS; TANDEM REACTION;

EID: 78650886604     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102217m     Document Type: Article
Times cited : (115)

References (59)
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    • For reviews on generation of acyliminium salts and reactions with nucleophiles including arenes, see
    • For reviews on generation of acyliminium salts and reactions with nucleophiles including arenes, see: Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367-4416
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    • 2-substituted arenes. For reviews, see
    • 2-substituted arenes. For reviews, see: Zaugg, H. E. Synthesis 1970, 49-73
    • (1970) Synthesis , pp. 49-73
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    • See also refs 2 and 4
    • Zaugg, H. E. Synthesis 1984, 181-212. See also refs 2 and 4
    • (1984) Synthesis , pp. 181-212
    • Zaugg, H.E.1
  • 9
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    • For reviews on anodic oxidation of organic compounds including alkylamides and synthetic applications of the oxidation products, see
    • For reviews on anodic oxidation of organic compounds including alkylamides and synthetic applications of the oxidation products, see: Shono, T. Tetrahedron 1984, 40, 811-850
    • (1984) Tetrahedron , vol.40 , pp. 811-850
    • Shono, T.1
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    • For examples of oxidation of alkylamides to α-oxyalkylamides, see
    • For examples of oxidation of alkylamides to α-oxyalkylamides, see: Mitani, M.; Watanabe, K.; Tachizawa, O.; Koyama, K. Chem. Lett. 1992, 21, 813-814
    • (1992) Chem. Lett. , vol.21 , pp. 813-814
    • Mitani, M.1    Watanabe, K.2    Tachizawa, O.3    Koyama, K.4
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    • As a part of extensive work on homolytic aromatic substitution (HAS), Minisci has reported the oxidative coupling of alkylamides with N -heteroarenes such as pyridine in the use of a peroxy oxidant including t -BuOO t -Bu, but the scope of arenes is limited to pyridine derivatives, which as protonated forms accept addition of nucleophilic acylaminomethyl radical intermediates.;, For a review on HAS:; Heterocycles 1989, 28, 489-519 For an iron-catalyzed reaction:; J. Chem. Soc., Chem. Commun. 1983, 916-917
    • As a part of extensive work on homolytic aromatic substitution (HAS), Minisci has reported the oxidative coupling of alkylamides with N -heteroarenes such as pyridine in the use of a peroxy oxidant including t -BuOO t -Bu, but the scope of arenes is limited to pyridine derivatives, which as protonated forms accept addition of nucleophilic acylaminomethyl radical intermediates. Arnone, A.; Cecere, M.; Galli, R.; Minisci, F.; Perchinunno, M.; Porta, O.; Gardini, G. Gazz. Chim. Ital. 1973, 103, 13-29 For a review on HAS: Minisci, F.; Vismara, E.; Fontana, F. Heterocycles 1989, 28, 489-519 For an iron-catalyzed reaction: Citterio, A.; Gentile, A.; Minisci, F.; Serravalle, M.; Ventura, S. J. Chem. Soc., Chem. Commun. 1983, 916-917
    • (1973) Gazz. Chim. Ital. , vol.103 , pp. 13-29
    • Arnone, A.1    Cecere, M.2    Galli, R.3    Minisci, F.4    Perchinunno, M.5    Porta, O.6    Gardini, G.7    Minisci, F.8    Vismara, E.9    Fontana, F.10    Citterio, A.11    Gentile, A.12    Minisci, F.13    Serravalle, M.14    Ventura, S.15
  • 19
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    • Fogg and dos Santos call this, in their review, "auto-tandem catalysis" with the definition "processes of this type involve two or more mechanistically distinct catalyses promoted by a single catalyst precursor: both cycles occur spontaneously by cooperative interaction of the various species (catalyst, substrate, additional reagents if required) present at the outset of reaction.", For other recent reviews on tandem catalysis, see:; Chem. Rev. 2005, 105, 1001-1020
    • Fogg and dos Santos call this, in their review, "auto-tandem catalysis" with the definition "processes of this type involve two or more mechanistically distinct catalyses promoted by a single catalyst precursor: both cycles occur spontaneously by cooperative interaction of the various species (catalyst, substrate, additional reagents if required) present at the outset of reaction." Fogg, D. E.; dos Santos, E. N. Coord. Chem. Rev. 2004, 248, 2365-2379 For other recent reviews on tandem catalysis, see: Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001-1020
    • (2004) Coord. Chem. Rev. , vol.248 , pp. 2365-2379
    • Fogg, D.E.1    Dos Santos, E.N.2    Wasilke, J.-C.3    Obrey, S.J.4    Baker, R.T.5    Bazan, G.C.6
  • 24
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    • Demethylation of N -methylamides through iron-catalyzed oxidation has been reported as a side reaction of homolytic aromatic substitution.
    • Demethylation of N -methylamides through iron-catalyzed oxidation has been reported as a side reaction of homolytic aromatic substitution. Citterio, A.; Gentile, A.; Minisci, F.; Serravalle, M.; Ventura, S. J. Org. Chem. 1984, 49, 3364-3367
    • (1984) J. Org. Chem. , vol.49 , pp. 3364-3367
    • Citterio, A.1    Gentile, A.2    Minisci, F.3    Serravalle, M.4    Ventura, S.5
  • 28
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    • Very recently, a report on iron-catalyzed oxdiative coupling of N -acyl-1,2,3,4-tetrahydroisoquinolines with indoles or polymethoxybenzenes appeared.;, For iron-catalyzed homo- and cross-coupling of alkylamines with arenes:; J. Chem. Soc., Chem. Commun. 1989, 116-118
    • Very recently, a report on iron-catalyzed oxdiative coupling of N -acyl-1,2,3,4-tetrahydroisoquinolines with indoles or polymethoxybenzenes appeared. Ghobrial, M.; Harhammer, K.; Mihovilovic, M. D.; Schnürch, M. Chem. Commun. 2010, 46, 8836-8838 For iron-catalyzed homo- and cross-coupling of alkylamines with arenes: Murata, S.; Miura, M.; Nomura, M. J. Chem. Soc., Chem. Commun. 1989, 116-118
    • (2010) Chem. Commun. , vol.46 , pp. 8836-8838
    • Ghobrial, M.1    Harhammer, K.2    Mihovilovic, M.D.3    Schnürch, M.4    Murata, S.5    Miura, M.6    Nomura, M.7
  • 30
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    • For oxidative couplings catalyzed by an iron(II) or iron(0) complex:; Angew. Chem., Int. Ed. 2007, 46, 6505-6507
    • Liu, P.; Zhou, C.-Y.; Xiang, S.; Che, C.-M. Chem. Commun. 2010, 46, 2739-2741 For oxidative couplings catalyzed by an iron(II) or iron(0) complex: Li, Z.; Cao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2007, 46, 6505-6507
    • (2010) Chem. Commun. , vol.46 , pp. 2739-2741
    • Liu, P.1    Zhou, C.-Y.2    Xiang, S.3    Che, C.-M.4    Li, Z.5    Cao, L.6    Li, C.-J.7
  • 36
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    • The reaction of 3m with 2a in the presence of HCl (1 mol %) under the same conditions (40 °C, 2 h, DCE) gave 4am in 2% yield (5% conv).
    • The reaction of 3m with 2a in the presence of HCl (1 mol %) under the same conditions (40 °C, 2 h, DCE) gave 4am in 2% yield (5% conv).
  • 37
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    • 2-catalyzed coupling of 1d with 3n, which is less nucleophilic than 3m, scored a lower yield (46%) under the same conditions as entry 6 of Table 3.
    • 2-catalyzed coupling of 1d with 3n, which is less nucleophilic than 3m, scored a lower yield (46%) under the same conditions as entry 6 of Table 3.
  • 40
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    • 2N(Me)Ac (0.22 mmol) in addition to 4du (2% yield) and the corresponding 2-indolyl isomer (5% yield)
    • 2N(Me)Ac (0.22 mmol) in addition to 4du (2% yield) and the corresponding 2-indolyl isomer (5% yield)
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    • Friedman, L.1    Shechter, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.