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Volumn 5, Issue 20, 2003, Pages 3607-3610

Cobalt-catalyzed arylation of azole heteroarenes via direct C-H bond functionalization

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBON; BENZIMIDAZOLE DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; BENZOXAZOLE DERIVATIVE; CESIUM; COBALT; IMIDAZOLE; IMIDAZOLE DERIVATIVE; OXAZOLE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRROLE DERIVATIVE; THIAZOLE DERIVATIVE; ZINC OXIDE;

EID: 0142106424     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035313o     Document Type: Article
Times cited : (111)

References (31)
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    • See also ref 2a
    • (b) See also ref 2a.
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    • (b) For solid-phase-assisted selective arylation of azoles: Kondo, Y.; Komine, T.; Sakamoto, T. Org. Lett. 2000, 2, 3111-3113.
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    • note
    • 1,3-Bis-mesitylimidazolium chloride is commercially available from Strem. It can also be prepared according to the procedure described in Arduengo, A. J., III (E. I. Du Pont de Nemours & Company), US 5.077.414 A2, 1992; WO 91/14678.
  • 14
    • 0142100405 scopus 로고    scopus 로고
    • note
    • In a typical procedure, anhydrous cobalt(II) acetate and the ligand were stirred at room temperature to form the active catalyst system, prior to the addition of the other reagents. This sequence of addition of ingredients proved to be important for the success of the method. For more detailed experimental procedures, see the Supporting Information.
  • 15
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    • note
    • These prices are quoted from the Aldrich Catalog, Aldrich, Milwaukee, WI, 2003.
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    • The indirect methods require lithiation and transmetalation to zinc (to prevent oxazole ring cleavage) prior to cross-coupling. Anderson, B. A.; Harn, N. K. Synthesis 1996, 583-585.
    • (1996) Synthesis , pp. 583-585
    • Anderson, B.A.1    Harn, N.K.2
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    • note
    • The mechanistic picture for the palladium-catalyzed arylation of heteroarenes has not been elucidated either. For discussion and references on this topic, see ref 3.
  • 24
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    • (e) Tsuji, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2002, 41, 4137-4139. Kneisel, F. F.; Monguchi, Y.; Knapp, K. M.; Zipse, H.; Knochel, P. Tetrahedron Lett. 2002, 43, 4875-4879.
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    • The effect of cobalt on the regiochemical course of intramolecular coupling between an aryl bromide and the pyridine ring has been observed. Harrowven, D. C.; Nunn, M. I. T.; Blumire, N. J.; Fenwick, D. R. Tetrahedron Lett. 2000, 41, 6681-6683.
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    • A metal-carbene intermediate should also be considered. For interesting reading on related topics, see: (a) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 3202-3203. (b) Gründemann, S.; Kovacevic, A.; Albrecht, M.; Faller, J. W.; Crabtree, R. H. J. Am. Chem. Soc. 2002, 124, 10473-10481.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 3202-3203
    • Tan, K.L.1    Bergman, R.G.2    Ellman, J.A.3
  • 31
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    • A metal-carbene intermediate should also be considered. For interesting reading on related topics, see: (a) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 3202-3203. (b) Gründemann, S.; Kovacevic, A.; Albrecht, M.; Faller, J. W.; Crabtree, R. H. J. Am. Chem. Soc. 2002, 124, 10473-10481.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10473-10481
    • Gründemann, S.1    Kovacevic, A.2    Albrecht, M.3    Faller, J.W.4    Crabtree, R.H.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.