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Volumn 12, Issue 15, 2010, Pages 3426-3429

Synthesis of fluoroazaindolines by an uncommon radical ipso substitution of a carbon-fluorine bond

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EID: 77955145613     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101240f     Document Type: Article
Times cited : (31)

References (43)
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    • We wish to acknowledge in this respect our collaboration on the theoretical aspects with Dr. Michelle Coote at the Australian National University
    • We wish to acknowledge in this respect our collaboration on the theoretical aspects with Dr. Michelle Coote at the Australian National University.
  • 4
    • 77955138229 scopus 로고    scopus 로고
    • For reviews on xanthate chemistry, see
    • For reviews on xanthate chemistry, see
  • 7
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    • Renaud, P.; Sibi, M. P., Eds. Wiley-VCH: Weinheim, Germany
    • Zard, S. Z. In Radical in Organic Chemistry; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, pp 90-108.
    • (2001) Radical in Organic Chemistry , vol.1 , pp. 90-108
    • Zard, S.Z.1
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    • Pentafluoropyridine usually reacts with amines first at the 4-position then at the 2-position. See for example
    • Pentafluoropyridine usually reacts with amines first at the 4-position then at the 2-position. See for example: Hargreaves, C. A.; Sanford, G.; Slater, R.; Yufit, D. S.; Howard, J. A. K.; Vong, A. Tetrahedron 2007, 63, 5204
    • (2007) Tetrahedron , vol.63 , pp. 5204
    • Hargreaves, C.A.1    Sanford, G.2    Slater, R.3    Yufit, D.S.4    Howard, J.A.K.5    Vong, A.6
  • 12
    • 77955170732 scopus 로고    scopus 로고
    • The reactivity of pentafluoropyridine and other fluorinated derivatives is extensively discussed in ref 6j
    • The reactivity of pentafluoropyridine and other fluorinated derivatives is extensively discussed in ref 6j.
  • 14
    • 62349095583 scopus 로고    scopus 로고
    • We thank one of the referees for pointing out this reference to us. β-Scission of chlorides, bromides, and iodides is well known: Struss, J. A.; Sadeghipour, M.; Tanko, J. M. Tetrahedron Lett. 2009, 50, 2119
    • (2009) Tetrahedron Lett. , vol.50 , pp. 2119
    • Struss, J.A.1    Sadeghipour, M.2    Tanko, J.M.3
  • 22
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    • For a review on C-F bond activation, see
    • For a review on C-F bond activation, see: Amii, H.; Uneyama, K. Chem. Rev. 2009, 109, 2119
    • (2009) Chem. Rev. , vol.109 , pp. 2119
    • Amii, H.1    Uneyama, K.2
  • 26
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    • Shoute and Mittal generated a radical-anion from hexafluorobenzene through radiolysis and noted the relative difficulty of eliminating a fluoride anion. Eliminating fluoride from a simple free radical should therefore be even more difficult. See
    • Shoute and Mittal generated a radical-anion from hexafluorobenzene through radiolysis and noted the relative difficulty of eliminating a fluoride anion. Eliminating fluoride from a simple free radical should therefore be even more difficult. See: Shoute, L. C. T.; Mittal, J. P. J. Phys. Chem. 1993, 97, 379
    • (1993) J. Phys. Chem. , vol.97 , pp. 379
    • Shoute, L.C.T.1    Mittal, J.P.2
  • 27
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    • Interestingly, these authors also remarked on the "considerable resistance" of hexafluorobenzene to radical addition. Both of these observations make our present cyclization and extrusion of a fluorine atom all the more unique
    • Interestingly, these authors also remarked on the "considerable resistance" of hexafluorobenzene to radical addition. Both of these observations make our present cyclization and extrusion of a fluorine atom all the more unique.
  • 28
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    • For an example of the use of high temperature to force a difficult cyclization on an aromatic ring, see
    • For an example of the use of high temperature to force a difficult cyclization on an aromatic ring, see: Quiclet-Sire, B.; Zard, S. Z. Chem. Commun. 2002, 2306
    • (2002) Chem. Commun. , pp. 2306
    • Quiclet-Sire, B.1    Zard, S.Z.2
  • 29
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    • The use of ring-fused trifluoropyridine systems in further synthetic transformations has recently been described. See for example
    • The use of ring-fused trifluoropyridine systems in further synthetic transformations has recently been described. See for example
  • 32
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    • For some very recent references, see
    • For some very recent references, see


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.