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Volumn 20, Issue 38, 2014, Pages 12190-12200

Harnessing the ortho-directing ability of the azetidine ring for the regioselective and exhaustive functionalization of arenes

Author keywords

azetidines; dynamic reactivity; heterocycles; lithiation; regioselectivity

Indexed keywords

AROMATIC COMPOUNDS; AROMATIZATION; ORGANOMETALLICS; REGIOSELECTIVITY;

EID: 84921360597     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201403141     Document Type: Article
Times cited : (35)

References (97)
  • 12
    • 84858028779 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2012, 51, 2722-2726
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 2722-2726
  • 16
  • 17
    • 22244435422 scopus 로고    scopus 로고
    • 1 (Ed.: Z. Rappoport), John Wiley & Sons: UK
    • J. Clayden, in Chemistry of Organolithium Compounds, Vol. 1 (Ed.:, Z. Rappoport,), John Wiley & Sons: UK, 2004, pp. 495-646
    • (2004) Chemistry of Organolithium Compounds , pp. 495-646
    • Clayden, J.1
  • 46
    • 0001068611 scopus 로고
    • For an example of chlorine-directed lithiation see
    • For an example of chlorine-directed lithiation see:, M. Iwao, J. Org. Chem. 1990, 55, 3622-3627.
    • (1990) J. Org. Chem. , vol.55 , pp. 3622-3627
    • Iwao, M.1
  • 47
    • 84925429845 scopus 로고    scopus 로고
    • Lithium amides can be employed in ortho-lithiations
    • Lithium amides can be employed in ortho-lithiations, see
  • 55
    • 84925429844 scopus 로고    scopus 로고
    • A similar competition has been reported for fluoroaryls that bear a methoxy substituent
    • A similar competition has been reported for fluoroaryls that bear a methoxy substituent, see
  • 73
    • 84884267338 scopus 로고    scopus 로고
    • H. Reich, Chem. Rev. 2013, 113, 7130-7178.
    • (2013) Chem. Rev. , vol.113 , pp. 7130-7178
    • Reich, H.1
  • 77
    • 0001651020 scopus 로고    scopus 로고
    • In the intermolecular KIE experiment, an effect of the ligand TMEDA was observed. The role of TMEDA is not well understood at the moment and a change in the mechanism for the H/Li permutation cannot be ruled out. For similar studies see:, However, structural studies by NMR spectroscopy, DOSY, and X-ray crystallography are underway, with the aim to shed light on this process and on the nature of the lithiated intermediates
    • In the intermolecular KIE experiment, an effect of the ligand TMEDA was observed. The role of TMEDA is not well understood at the moment and a change in the mechanism for the H/Li permutation cannot be ruled out. For similar studies see:, M. Stratakis, J. Org. Chem. 1997, 62, 3024-3025. However, structural studies by NMR spectroscopy, DOSY, and X-ray crystallography are underway, with the aim to shed light on this process and on the nature of the lithiated intermediates.
    • (1997) J. Org. Chem. , vol.62 , pp. 3024-3025
    • Stratakis, M.1
  • 86
    • 80054847382 scopus 로고    scopus 로고
    • Example of preferential conformations in substituted aziridines have been recently reported by us
    • Example of preferential conformations in substituted aziridines have been recently reported by us:, M. C. de Ceglie, L. Degennaro, A. Falcicchio, R. Luisi, Tetrahedron 2011, 67, 9382-9388.
    • (2011) Tetrahedron , vol.67 , pp. 9382-9388
    • De Ceglie, M.C.1    Degennaro, L.2    Falcicchio, A.3    Luisi, R.4
  • 93
    • 0032541271 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1998, 37, 1986-2012.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1986-2012


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.