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Volumn 9, Issue 12, 2007, Pages 2333-2336

Direct Pd-catalyzed arylation of 1,2,3-triazoles

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; TRIAZOLE DERIVATIVE;

EID: 34250864418     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070697u     Document Type: Article
Times cited : (220)

References (37)
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    • (a) Fan, W.-Q.; Katritzky, A. R. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier: Oxford, UK, 1996; Vol. 4, pp 1-126.
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    • Fan, W.-Q.1    Katritzky, A.R.2
  • 7
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    • Product class 13: 1,2,3-triazoles
    • Stor, R, Gilchrist, T, Eds, Thieme: New York
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    • Tome, A.C.1
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    • (a) Padwa, A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, UK, 1991; Vol. 4, pp 1069-1109.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1069-1109
    • Padwa, A.1
  • 13
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    • and references therein
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    • (1969) Ind. Chim. Belge , vol.34 , pp. 519
    • L'Abbè, G.1
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    • For recent reviews, see: a, DOI: 10.1039/b606984n
    • For recent reviews, see: (a) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, DOI: 10.1039/b606984n.
    • Chem. Soc. Rev , vol.2007
    • Seregin, I.V.1    Gevorgyan, V.2
  • 23
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    • For intramolecular Heck-type vinylation of 1,2,3-triazole, see: Chen, W.-L.; Su, C.-L.; Huang, X. Synlett 2006, 1446.
    • For intramolecular Heck-type vinylation of 1,2,3-triazole, see: Chen, W.-L.; Su, C.-L.; Huang, X. Synlett 2006, 1446.
  • 25
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    • Notably, we did not observe triazole-directed arylation of N-aryl or W-benzyl substitutents under these reaction conditions. For amide- and heterocycle-directed arylation of arenes via C-H activation, see, for example: (a) Shabashov, D.; Daugulis, O. Org. Lett. 2005, 7, 3657.
    • Notably, we did not observe triazole-directed arylation of N-aryl or W-benzyl substitutents under these reaction conditions. For amide- and heterocycle-directed arylation of arenes via C-H activation, see, for example: (a) Shabashov, D.; Daugulis, O. Org. Lett. 2005, 7, 3657.
  • 28
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    • Fundamental differences in C-5 and C-4 reactivity of 1,2,3-triazoles are also observed during lithiation reactions. See, for example: (a) Grimmett, M. R.; Iddon, B. Heterocycles 1995, 41, 1525.
    • Fundamental differences in C-5 and C-4 reactivity of 1,2,3-triazoles are also observed during lithiation reactions. See, for example: (a) Grimmett, M. R.; Iddon, B. Heterocycles 1995, 41, 1525.
  • 31
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    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 35
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    • For a detailed discussion of these mechanisms, see refs 11a and 14. See also: Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050.
    • For a detailed discussion of these mechanisms, see refs 11a and 14. See also: Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050.
  • 36
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    • For a discussion on the electrophilic mechanism in the arylation of heterocycles, see refs 19, 21, and 12
    • For a discussion on the electrophilic mechanism in the arylation of heterocycles, see refs 19, 21, and 12.
  • 37
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    • Although nearly equal reactivity of 1a vs 1g is not clearly understood, a similar trend was observed in cationic Heck reactions in the styrene series krel p-OMe:H:p-CO2Me, 1.21:1.00:0.96, see: Fristrup, P, Le Quement, S, Tanner, D, Norrby, P.-O. Organometallics 2004, 23, 6160
    • 2Me = 1.21:1.00:0.96), see: Fristrup, P.; Le Quement, S.; Tanner, D.; Norrby, P.-O. Organometallics 2004, 23, 6160.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.