메뉴 건너뛰기




Volumn 53, Issue 42, 2014, Pages 11333-11337

Trans-Selective Radical Silylzincation of Ynamides

Author keywords

copper; radical reactions; silicon; silylmetalation; zinc

Indexed keywords

COPPER; REACTION KINETICS; SILICON;

EID: 85028250164     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201407002     Document Type: Article
Times cited : (67)

References (51)
  • 1
    • 84859100554 scopus 로고    scopus 로고
    • For an authoritative review of vinylic silanes, see.
    • For an authoritative review of vinylic silanes, see:, D. S. W. Lim, E. A. Anderson, Synthesis 2012, 983-1010.
    • (2012) Synthesis , pp. 983-1010
    • Lim, D.S.W.1    Anderson, E.A.2
  • 5
    • 6944249016 scopus 로고    scopus 로고
    • for the original work, see
    • A. Barbero, F. J. Pulido, Acc. Chem. Res. 2004, 37, 817-825; for the original work, see:
    • (2004) Acc. Chem. Res. , vol.37 , pp. 817-825
    • Barbero, A.1    Pulido, F.J.2
  • 14
    • 40549085002 scopus 로고    scopus 로고
    • Stereoselective access to E-2-borylated vinylic silanes by Z-to-E isomerization was reported in one case.
    • Stereoselective access to E-2-borylated vinylic silanes by Z-to-E isomerization was reported in one case:, T. Ohmura, K. Oshima, M. Suginome, Chem. Commun. 2008, 1416-1418.
    • (2008) Chem. Commun. , pp. 1416-1418
    • Ohmura, T.1    Oshima, K.2    Suginome, M.3
  • 17
    • 84907832151 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 4238-4242;
    • (2014) Angew. Chem. , vol.126 , pp. 4238-4242
  • 19
    • 84907832150 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 4243-4247.
    • (2014) Angew. Chem. , vol.126 , pp. 4243-4247
  • 25
    • 84907811614 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 10268-10272;
    • (2013) Angew. Chem. , vol.125 , pp. 10268-10272
  • 34
    • 0033832150 scopus 로고    scopus 로고
    • Organosilyl radical addition to CC bonds following UV irradiation of organosilylboranes was reported.
    • Organosilyl radical addition to C C bonds following UV irradiation of organosilylboranes was reported:, A. Matsumoto, Y. Ito, J. Org. Chem. 2000, 65, 5707-5711.
    • (2000) J. Org. Chem. , vol.65 , pp. 5707-5711
    • Matsumoto, A.1    Ito, Y.2
  • 36
    • 84942299960 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 4749-4753.
    • (2012) Angew. Chem. , vol.124 , pp. 4749-4753
  • 38
    • 62349134364 scopus 로고    scopus 로고
    • For a related radical addition of thiyl radicals, see.
    • For a related radical addition of thiyl radicals, see:, A. Sato, H. Yorimitsu, K. Oshima, Synlett 2009, 28-31.
    • (2009) Synlett , pp. 28-31
    • Sato, A.1    Yorimitsu, H.2    Oshima, K.3
  • 40
    • 33746041777 scopus 로고    scopus 로고
    • 2Zn, see:, the β-elimination had been observed by us previously
    • 2Zn, see:, G. Auer, B. Weiner, M. Oestreich, Synthesis 2006, 2113-2116; the β-elimination had been observed by us previously:
    • (2006) Synthesis , pp. 2113-2116
    • Auer, G.1    Weiner, B.2    Oestreich, M.3
  • 42
    • 85028267913 scopus 로고    scopus 로고
    • I-catalyzed carbo- and hydrozincation of ynamides, was engaged in Negishi cross-coupling reactions by Lam and co-workers
    • I-catalyzed carbo- and hydrozincation of ynamides, was engaged in Negishi cross-coupling reactions by Lam and co-workers:
  • 45
    • 85028254041 scopus 로고    scopus 로고
    • CCDC 1009934 (Z- 13), 1009935 (Z- 27) and 1009936 (E- 30) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
    • CCDC 1009934 (Z- 13), 1009935 (Z- 27) and 1009936 (E- 30) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
  • 46
    • 42749092334 scopus 로고    scopus 로고
    • 2 as an additive:, These reaction conditions were not compatible with our enamides and led to protodesilylation.
    • 2 as an additive:, Z. Wang, J.-P. Pitteloud, L. Montes, M. Rapp, D. Derane, S. F. Wnuk, Tetrahedron 2008, 64, 5322-5327. These reaction conditions were not compatible with our enamides and led to protodesilylation.
    • (2008) Tetrahedron , vol.64 , pp. 5322-5327
    • Wang, Z.1    Pitteloud, J.-P.2    Montes, L.3    Rapp, M.4    Derane, D.5    Wnuk, S.F.6
  • 47
    • 85028241309 scopus 로고    scopus 로고
    • The reasons for this inversion are not clear but may be the result of a participating effect of the Lewis basic bromine atom introduced in allylic position prior to the bromodesilylation reaction.
    • The reasons for this inversion are not clear but may be the result of a participating effect of the Lewis basic bromine atom introduced in allylic position prior to the bromodesilylation reaction.
  • 48
    • 85028234212 scopus 로고    scopus 로고
    • For recent applications of α-carbonyl β-substituted enamides, see
    • For recent applications of α-carbonyl β-substituted enamides, see:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.