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Volumn 74, Issue 24, 2009, Pages 9570-9572

Copper-catalyzed synthesis of 2-unsubstituted, N-substituted benzimidazoles

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; BENZIMIDAZOLES; CATALYZED SYNTHESIS; CHEMICAL EQUATIONS; FORMAMIDINES; STERICALLY DEMANDING;

EID: 73149121933     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902160y     Document Type: Article
Times cited : (70)

References (65)
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    • Nolan, S. P, Ed, Wiley-VCH: Weinheim, Germany
    • (d) Nolan, S. P., Ed. N-Heterocyclic Carbenes in Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
    • (2006) N-Heterocyclic Carbenes in Synthesis
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    • For some of our key papers on the design and application of NHC-ligands, see: a
    • For some of our key papers on the design and application of NHC-ligands, see: (a) Würtz, S.; Lohre, C.; Fröhlich, R.; Bergander, K.; Glorius, F. J. Am. Chem. Soc. 2009, 131, 8344.
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  • 22
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    • For some recent reports, see: a
    • For some recent reports, see: (a) Prasad, B. A. B.; Gilbertson, S. R. Org. Lett. 2009, 11, 3710.
    • (2009) Org. Lett , vol.11 , pp. 3710
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    • 2d.
    • 2d.
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    • For the successful application of N-mesityl-N′- methylbenzimidazolium iodide as NHC precursor in organocatalytic umpolung reactions, see: Chan, A.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 5334.
    • For the successful application of N-mesityl-N′- methylbenzimidazolium iodide as NHC precursor in organocatalytic umpolung reactions, see: Chan, A.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 5334.
  • 45
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    • Rivas, F. M.; Riaz, U.; Giessert, A.; Smulik, J. A.; Diver, S. T. Org. Lett. 2001, 3, 2673. See also refs 8e and 8g.
    • (b) Rivas, F. M.; Riaz, U.; Giessert, A.; Smulik, J. A.; Diver, S. T. Org. Lett. 2001, 3, 2673. See also refs 8e and 8g.
  • 46
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    • A Beilstein Crossfire search on the 30th of August 2009 revealed only 11 entries for the formation of benzimidazolium salts from substituted 1,2-diamino arenes, whereas the alkylation (including activated alkyl groups like benzyl or α-carbonyl) of benzimidazoles was found 322 times.
    • A Beilstein Crossfire search on the 30th of August 2009 revealed only 11 entries for the formation of benzimidazolium salts from substituted 1,2-diamino arenes, whereas the alkylation (including activated alkyl groups like benzyl or α-carbonyl) of benzimidazoles was found 322 times.
  • 49
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    • For the direct synthesis of benzimidazolium salts from dihydropyridines and isocyanides, see
    • For the direct synthesis of benzimidazolium salts from dihydropyridines and isocyanides, see: Masdeu, C.; Gómez, E.; Williams, N. A. O.; Lavilla, R. Angew. Chem., Int. Ed. 2007, 46, 3043.
    • (2007) Angew. Chem., Int. Ed , vol.46 , pp. 3043
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  • 60
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    • For another synthetic route employing only one palladium-catalyzed reaction, starting from 1-bromo-2-nitrobenzene, see
    • For another synthetic route employing only one palladium-catalyzed reaction, starting from 1-bromo-2-nitrobenzene, see: Duan, W.-L.; Shi, M.; Rong, G.-B. Chem. Commun. 2003, 2916.
    • (2003) Chem. Commun , pp. 2916
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    • For convenience, 20 mol % of CuI was used under standard conditions. See the Supporting Information for further details.
    • For convenience, 20 mol % of CuI was used under standard conditions. See the Supporting Information for further details.
  • 65
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    • Very recently, a related paper on the 'Synthesis of 1-Substituted Benzimidazoles from o-Bromophenyl Isocyanide and Amines' appeared: Lygin, A. V.; de Meijere, A. Eur. J. Org. Chem. 2009, 5138-5141.
    • Very recently, a related paper on the 'Synthesis of 1-Substituted Benzimidazoles from o-Bromophenyl Isocyanide and Amines' appeared: Lygin, A. V.; de Meijere, A. Eur. J. Org. Chem. 2009, 5138-5141.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.