메뉴 건너뛰기




Volumn 44, Issue 12, 2005, Pages 1870-1873

Erratum: Synthesis of medium-ring and iodinated biaryl compounds by organocuprate oxidation (Angewandte Chemie International Edition (2005) 44 (1870-1873) DOI: 10.1002/anie.200462642);Synthesis of medium-ring and iodinated biaryl compounds by organocuprate oxidation

Author keywords

Biaryls; C C coupling; Medium ring compounds; Organocuprates; Oxidation

Indexed keywords

OXIDATION; SYNTHESIS (CHEMICAL);

EID: 17044379486     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462642     Document Type: Erratum
Times cited : (56)

References (52)
  • 2
    • 0000658001 scopus 로고    scopus 로고
    • For the palladium-catalyzed dimerization of aryl halides, see: a) D. D. Hennings, T. Iwama, V. H. Rawal, Org. Lett. 1999, 1, 1205; b) J. Hassan, V. Penalva, L. Lavenot, C. Gozzi, M. Lemaire, Tetrahedron 1998, 54, 13793; c) F.-T. Luo, A. Jeevanandam, M. K. Basu, Tetrahedron Lett. 1998, 39, 7939.
    • (1999) Org. Lett. , vol.1 , pp. 1205
    • Hennings, D.D.1    Iwama, T.2    Rawal, V.H.3
  • 3
    • 0032487938 scopus 로고    scopus 로고
    • For the palladium-catalyzed dimerization of aryl halides, see: a) D. D. Hennings, T. Iwama, V. H. Rawal, Org. Lett. 1999, 1, 1205; b) J. Hassan, V. Penalva, L. Lavenot, C. Gozzi, M. Lemaire, Tetrahedron 1998, 54, 13793; c) F.-T. Luo, A. Jeevanandam, M. K. Basu, Tetrahedron Lett. 1998, 39, 7939.
    • (1998) Tetrahedron , vol.54 , pp. 13793
    • Hassan, J.1    Penalva, V.2    Lavenot, L.3    Gozzi, C.4    Lemaire, M.5
  • 4
    • 0032558674 scopus 로고    scopus 로고
    • For the palladium-catalyzed dimerization of aryl halides, see: a) D. D. Hennings, T. Iwama, V. H. Rawal, Org. Lett. 1999, 1, 1205; b) J. Hassan, V. Penalva, L. Lavenot, C. Gozzi, M. Lemaire, Tetrahedron 1998, 54, 13793; c) F.-T. Luo, A. Jeevanandam, M. K. Basu, Tetrahedron Lett. 1998, 39, 7939.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7939
    • Luo, F.-T.1    Jeevanandam, A.2    Basu, M.K.3
  • 5
    • 17044438702 scopus 로고    scopus 로고
    • Ed.: F. Diederich, P. J. Stang, Wiley-VCH, New York, chap. 4
    • For palladium-catalyzed cross-coupling reactions, see: a) T. N. Mitchell in Metal-Catalyzed Cross-Coupling Reactions (Ed.: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998, chap. 4; b) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; c) E. Negishi, Acc. Chem. Res. 1982, 15, 340.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions
    • Mitchell, T.N.1
  • 6
    • 2042507954 scopus 로고
    • For palladium-catalyzed cross-coupling reactions, see: a) T. N. Mitchell in Metal-Catalyzed Cross-Coupling Reactions (Ed.: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998, chap. 4; b) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; c) E. Negishi, Acc. Chem. Res. 1982, 15, 340.
    • (1995) Chem. Rev. , vol.95 , pp. 2457
    • Miyaura, N.1    Suzuki, A.2
  • 7
    • 33750026643 scopus 로고
    • For palladium-catalyzed cross-coupling reactions, see: a) T. N. Mitchell in Metal-Catalyzed Cross-Coupling Reactions (Ed.: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998, chap. 4; b) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; c) E. Negishi, Acc. Chem. Res. 1982, 15, 340.
    • (1982) Acc. Chem. Res. , vol.15 , pp. 340
    • Negishi, E.1
  • 13
    • 0037118887 scopus 로고    scopus 로고
    • a) Oxidative coupling, for example: B. Kramer, A. Averhoff, S. R. Waldvogel, Angew. Chem. 2002, 114, 3103; Angew. Chem. Int. Ed. 2002, 41, 2981;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2981
  • 32
    • 33748214746 scopus 로고
    • a) B. H. Lipshutz, F. Kayser, Z.-P. Liu, Angew. Chem. 1994, 106, 1962; Angew. Chem. Int. Ed. Engl. 1994, 33, 1844;
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1844
  • 38
    • 17044373648 scopus 로고    scopus 로고
    • note
    • CuCN, CuSCN, and CuI gave comparable but lower yields.
  • 40
    • 17044408033 scopus 로고    scopus 로고
    • note
    • 4, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), and potassium nitrosodisulfonate (Fremy's salt), gave unsatisfactory yields.
  • 41
    • 17044439160 scopus 로고    scopus 로고
    • note
    • This compound is readily synthesized in high yield on a large scale from commercially available starting materials (see the Supporting Information) and can be stored indefinitely at room temperature.
  • 42
    • 17044409738 scopus 로고
    • The dianion of dinitrobenzene has been studied electrochemically; for an example see: H. Wang, V. D. Parker, Acta Chem. Scand. 1994, 48, 933.
    • (1994) Acta Chem. Scand. , vol.48 , pp. 933
    • Wang, H.1    Parker, V.D.2
  • 43
    • 17044391900 scopus 로고    scopus 로고
    • note
    • An alternative possibility is that the biphenyl product can itself act as a single-electron oxidant; however, this possibility was ruled out as biphenyl did not act as an oxidant in control reactions.
  • 44
    • 4644300966 scopus 로고    scopus 로고
    • It has recently been found that this dimerization proceeds in only moderate yield in a palladium-catalyzed system, see: C. F. Nising, U. K. Schmid, M. Nieger, S. Bräse, J. Org. Chem. 2004, 69, 6830.
    • (2004) J. Org. Chem. , vol.69 , pp. 6830
    • Nising, C.F.1    Schmid, U.K.2    Nieger, M.3    Bräse, S.4
  • 45
    • 14744285625 scopus 로고    scopus 로고
    • The halogen-metal exchange has recently been extended to allow the formation of aryl magnesium compounds from the corresponding aryl bromides: A. Krasovskiy, P. Knochel, Angew. Chem. 2004, 116, 3396; Angew. Chem. Int. Ed. 2004, 43, 3333. Our preliminary investigations suggest that Grignard reagents formed in this way may also be used to form organocuprates, which may be successfully oxidized under our conditions.
    • (2004) Angew. Chem. , vol.116 , pp. 3396
    • Krasovskiy, A.1    Knochel, P.2
  • 46
    • 4544311534 scopus 로고    scopus 로고
    • The halogen-metal exchange has recently been extended to allow the formation of aryl magnesium compounds from the corresponding aryl bromides: A. Krasovskiy, P. Knochel, Angew. Chem. 2004, 116, 3396; Angew. Chem. Int. Ed. 2004, 43, 3333. Our preliminary investigations suggest that Grignard reagents formed in this way may also be used to form organocuprates, which may be successfully oxidized under our conditions.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 3333


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.