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Volumn 75, Issue 15, 2010, Pages 4911-4920

C-H bonds as ubiquitous functionality: A general approach to complex arylated imidazoles via regioselective sequential arylation of all three C-H bonds and regioselective n -alkylation enabled by SEM-group transposition

Author keywords

[No Author keywords available]

Indexed keywords

ARYL BROMIDES; ARYL CHLORIDE; ARYLATIONS; C-H BOND; CHLOROARENES; DEPROTECTION; DRUG CANDIDATES; FUNCTIONALIZED; GENERAL APPROACH; HETEROCYCLES; HETEROCYCLIC RINGS; IMIDAZOLE DERIVATIVES; LABORATORY CONDITIONS; N-ALKYLATION; POSITIONAL SELECTIVITY; REGIO-SELECTIVE; SEM; TRANSITION METAL CATALYSTS; TRIARYL IMIDAZOLE;

EID: 77955137089     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100727j     Document Type: Article
Times cited : (145)

References (73)
  • 11
    • 20844451096 scopus 로고    scopus 로고
    • Thieme: Stuttgart
    • Science of Synthesis; Grimmett, M. R., Ed.; Thieme: Stuttgart, 2002; Vol. 12, pp 325 - 512.
    • (2002) Science of Synthesis , vol.12 , pp. 325-512
    • Grimmett, M.R.1
  • 19
    • 33645674829 scopus 로고    scopus 로고
    • For global analysis of approaches toward C-H bond functionalization and its consequences in organic synthesis, see
    • For global analysis of approaches toward C-H bond functionalization and its consequences in organic synthesis, see: Godula, K.; Sames, D. Science 2006, 312, 67-72
    • (2006) Science , vol.312 , pp. 67-72
    • Godula, K.1    Sames, D.2
  • 20
    • 0242526099 scopus 로고    scopus 로고
    • Recent reviews on catalytic C-H bond functionalization
    • Recent reviews on catalytic C-H bond functionalization: Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077-1101
    • (2003) Adv. Synth. Catal. , vol.345 , pp. 1077-1101
    • Kakiuchi, F.1    Chatani, N.2
  • 30
    • 70350780276 scopus 로고    scopus 로고
    • A comprehensive review on arylation of heteroarenes including azoles
    • A comprehensive review on arylation of heteroarenes including azoles: Bellina, F.; Rossi, R. Tetrahedron 2009, 65, 10269-10310
    • (2009) Tetrahedron , vol.65 , pp. 10269-10310
    • Bellina, F.1    Rossi, R.2
  • 31
    • 70349972667 scopus 로고    scopus 로고
    • Since the publication of this review, C5-arylation of 1-alkylimidazoles with aryl bromides has been reported
    • Since the publication of this review, C5-arylation of 1-alkylimidazoles with aryl bromides has been reported: Roger, J.; Doucet, H. Tetrahedron 2009, 65, 9772-9781
    • (2009) Tetrahedron , vol.65 , pp. 9772-9781
    • Roger, J.1    Doucet, H.2
  • 32
  • 37
    • 62849102089 scopus 로고    scopus 로고
    • For recent examples of catalytic C-H arylation of arenes and heteroarenes, see
    • For recent examples of catalytic C-H arylation of arenes and heteroarenes, see: Phipps, R. J.; Gaunt, M. J. Science 2009, 323, 1593-1597
    • (2009) Science , vol.323 , pp. 1593-1597
    • Phipps, R.J.1    Gaunt, M.J.2
  • 41
    • 43849101552 scopus 로고    scopus 로고
    • Synthesis of diarylimidazoles via sequential arylation of N -benzylimidazoles has been reported
    • Synthesis of diarylimidazoles via sequential arylation of N -benzylimidazoles has been reported: Bellina, F.; Cauteruccio, S.; Fiore, A. D.; Marchetti, C.; Rossi, R. Tetrahedron 2008, 64, 6060-6072
    • (2008) Tetrahedron , vol.64 , pp. 6060-6072
    • Bellina, F.1    Cauteruccio, S.2    Fiore, A.D.3    Marchetti, C.4    Rossi, R.5
  • 43
    • 77955165374 scopus 로고    scopus 로고
    • For recent examples of sequential arylation to produce highly substituted heteroarenes, see: Ref 15 a
    • For recent examples of sequential arylation to produce highly substituted heteroarenes, see: Ref 15 a.
  • 49
    • 34247489285 scopus 로고    scopus 로고
    • C5-Arylation of N -butylimidazole with chlorobenzene (in 52% yield) was reported
    • C5-Arylation of N -butylimidazole with chlorobenzene (in 52% yield) was reported: Chiong, H. A.; Daugulis, O. Org. Lett. 2007, 9, 1449-1451
    • (2007) Org. Lett. , vol.9 , pp. 1449-1451
    • Chiong, H.A.1    Daugulis, O.2
  • 52
    • 77955124890 scopus 로고    scopus 로고
    • For other examples of C2-arylation of N -methylimidazole using the Pd/CuI system, see the comprehensive review in ref 16a
    • For other examples of C2-arylation of N -methylimidazole using the Pd/CuI system, see the comprehensive review in ref 16a.
  • 53
    • 57349113866 scopus 로고    scopus 로고
    • Copper-catalyzed C2-arylation of N -methylimidazole with iodobenzene has been reported
    • Copper-catalyzed C2-arylation of N -methylimidazole with iodobenzene has been reported: Do, H.-Q.; Khan, R. M. K.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 15185-15192
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 15185-15192
    • Do, H.-Q.1    Khan, R.M.K.2    Daugulis, O.3
  • 60
    • 84855637600 scopus 로고    scopus 로고
    • 3 C-H arylation of α-methyl azine- N -oxides, a method that also depends on the use of NaO t -Bu as the base (see ref 31). The authors proposed that the catalyst was inhibited by cyclopalladation of the products containing relatively acidic benzylic groups. It is conceivable that in our case cyclopalladation of the 2′-position of the aryl ring may sequester the palladium catalyst. Inhibition by direct coordination of the nitrile group to the palladium metal is also possible; however, processes responsible for the catalyst deactivation are presently not known
    • 3 C-H arylation of α-methyl azine- N -oxides, a method that also depends on the use of NaO t -Bu as the base (see ref 31). The authors proposed that the catalyst was inhibited by cyclopalladation of the products containing relatively acidic benzylic groups. It is conceivable that in our case cyclopalladation of the 2′-position of the aryl ring may sequester the palladium catalyst. Inhibition by direct coordination of the nitrile group to the palladium metal is also possible; however, processes responsible for the catalyst deactivation are presently not known.
  • 62
    • 84855618279 scopus 로고    scopus 로고
    • 2, 3-bromoanisole, and NaO t -Bu in toluene in 84% isolated yield
    • 2, 3-bromoanisole, and NaO t -Bu in toluene in 84% isolated yield.
  • 65
    • 0038666538 scopus 로고    scopus 로고
    • A report on the exchange of a SEM group with a benzyl group in the context of 4-arylimidazole synthesis
    • A report on the exchange of a SEM group with a benzyl group in the context of 4-arylimidazole synthesis: Nakamura, S.; Kawasaki, I.; Yamashita, M.; Ohta, S. Heterocycles 2003, 60, 583-598
    • (2003) Heterocycles , vol.60 , pp. 583-598
    • Nakamura, S.1    Kawasaki, I.2    Yamashita, M.3    Ohta, S.4
  • 66
    • 84855636020 scopus 로고    scopus 로고
    • The palladium-catalyzed C5-arylation of 1-benzylimidazoles has been reported (see ref 19). Similar to the SEM group transposition, the benzyl group should be transposable in the presence of a catalytic amount of benzyl bromide. In fact, 1-benzyl-5-phenylimidazole, obtained in 72% isolated yield through our protocol, underwent a benzyl switch to give 1-benzyl-4-phenylimidazole 39 in 84% isolated yield; however, the reaction required extended heating (5 days in DMF at 140 °C)
    • The palladium-catalyzed C5-arylation of 1-benzylimidazoles has been reported (see ref 19). Similar to the SEM group transposition, the benzyl group should be transposable in the presence of a catalytic amount of benzyl bromide. In fact, 1-benzyl-5-phenylimidazole, obtained in 72% isolated yield through our protocol, underwent a benzyl switch to give 1-benzyl-4-phenylimidazole 39 in 84% isolated yield; however, the reaction required extended heating (5 days in DMF at 140 °C).
  • 69
    • 34547636188 scopus 로고    scopus 로고
    • Catalytic N -arylation of imidazoles with aryl halides:;;, and references therein
    • Catalytic N -arylation of imidazoles with aryl halides: Altman, R. A.; Koval, E. D.; Buchwald, S. L. J. Org. Chem. 2007, 72, 6190-6199 and references therein.
    • (2007) J. Org. Chem. , vol.72 , pp. 6190-6199
    • Altman, R.A.1    Koval, E.D.2    Buchwald, S.L.3


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