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Volumn 12, Issue 2, 2010, Pages 368-371

Electron transfer photoredox catalysis: Intramolecular radical addition to indoles and pyrroles

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EID: 74949084706     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902703k     Document Type: Article
Times cited : (293)

References (46)
  • 4
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  • 9
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    • For examples of functional group reactivity using other radical initiation systems, see: (a) Ferris, J. P.; Antonucci, F. R. J. Am. Chem. Soc. 1972, 94, 8091.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 8091
    • Ferris, J.P.1    Antonucci, F.R.2
  • 13
  • 16
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    • For the use of dihydroacridines as a hydrogen atom source for the reduction of α-haloacetophenones using Ru-mediated photoredox catalysis, see: Fukuzumi, S.; Mochizuki, S.; Tanaka, T. J. Phys. Chem. 1990, 94, 722.
    • (1990) J. Phys. Chem. , vol.94 , pp. 722
    • Fukuzumi, S.1    Mochizuki, S.2    Tanaka, T.3
  • 19
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    • For reviews on the photoactivation of metal complexes, see: (a) Salomon, R. G. Tetrahedron 1983, 39, 485.
    • (1983) Tetrahedron , vol.39 , pp. 485
    • Salomon, R.G.1
  • 29
    • 33947602410 scopus 로고    scopus 로고
    • For selected recent examples of the functionalization of indoles and pyrroles, see: (a) Baran, P. S.; Maimone, T. J.; Richter, J. M. Nature 2007, 446, 404.
    • (2007) Nature , vol.446 , pp. 404
    • Baran, P.S.1    Maimone, T.J.2    Richter, J.M.3
  • 34
    • 7044286458 scopus 로고    scopus 로고
    • For an excellent review on Mn(III) chemistry, see: Snider, B. B. Chem. Rev. 1996, 96, 339.
    • (1996) Chem. Rev. , vol.96 , pp. 339
    • Snider, B.B.1
  • 35
    • 0027751857 scopus 로고
    • For selected examples of radical initiated methods of indole/pyrrole functionalization, see: (a) Baciocchi, E.; Muragli, E. J. Org. Chem. 1993, 58, 7610.
    • (1993) J. Org. Chem. , vol.58 , pp. 7610
    • Baciocchi, E.1    Muragli, E.2
  • 41
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    • 1H NMR, present as an approximately 1:1 mixture with the cyclized product
    • 1H NMR, present as an approximately 1:1 mixture with the cyclized product.
  • 44
    • 74949108501 scopus 로고    scopus 로고
    • See the Supporting Information for the preparation of 4
    • See the Supporting Information for the preparation of 4.
  • 45
    • 74949118733 scopus 로고    scopus 로고
    • The relative configuration of the product was determined by X-ray crystallographic analysis. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre (CCDC 748503) via
    • The relative configuration of the product was determined by X-ray crystallographic analysis. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre (CCDC 748503) via www. ccdc.cam.ac.uk/data-request/cif.
  • 46
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    • Oxidation via the action of adventitious oxygen or trialkylammonium radical cations cannot be ruled out at this time
    • MacMillan and coworkers have previously postulated the oxdiation of α-aminylradicals by the Ru(II) excited state (see refs 10a and .10f). For a discussion on electron recycling in catalysis, see: Buckel, W. Angew. Chem., Int. Ed. 2009, 48, 6779. Oxidation via the action of adventitious oxygen or trialkylammonium radical cations cannot be ruled out at this time.
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 6779
    • Buckel, W.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.