메뉴 건너뛰기




Volumn 53, Issue 37, 2014, Pages 9817-9821

Chemoselective carbophilic addition of α-diazoesters through ligand-controlled gold catalysis

Author keywords

carbenoids; carbocations; carbophilicity; diazo compounds; gold

Indexed keywords

CATALYSIS; CATALYSTS; CHEMICAL COMPOUNDS; KETONES; LIGANDS;

EID: 84906947831     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201404946     Document Type: Article
Times cited : (242)

References (89)
  • 28
    • 84899862031 scopus 로고    scopus 로고
    • for related examples, see
    • Angew. Chem. Int. Ed. 2014, 53, 4807; for related examples, see
    • (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 4807
  • 32
    • 84900807376 scopus 로고    scopus 로고
    • While this manuscript was under review, a similar study was reported.
    • While this manuscript was under review, a similar study was reported:, Z. Yu, B. Ma, M. Chen, H.-H. Wu, L. Liu, J. Zhang, J. Am. Chem. Soc. 2014, 136, 6904.
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 6904
    • Yu, Z.1    Ma, B.2    Chen, M.3    Wu, H.-H.4    Liu, L.5    Zhang, J.6
  • 37
    • 79959788014 scopus 로고    scopus 로고
    • For an instructive review, see.
    • For an instructive review, see:, H. M. L. Davies, D. Mortona, Chem. Soc. Rev. 2011, 40, 1857.
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 1857
    • Davies, H.M.L.1    Mortona, D.2
  • 38
    • 84906949990 scopus 로고    scopus 로고
    • For an instructive review, see
    • For an instructive review, see
  • 58
    • 78650137928 scopus 로고    scopus 로고
    • A similar aromatic substitution with diazo compounds has been described with copper catalysts; however, only a very limited scope was reported.
    • A similar aromatic substitution with diazo compounds has been described with copper catalysts; however, only a very limited scope was reported:, E. Tayama, T. Yanaki, H. Iwamoto, E. Hasegawa, Eur. J. Org. Chem. 2010, 6719.
    • (2010) Eur. J. Org. Chem. , pp. 6719
    • Tayama, E.1    Yanaki, T.2    Iwamoto, H.3    Hasegawa, E.4
  • 70
    • 84906949992 scopus 로고    scopus 로고
    • The typical metal-catalyzed α-diazoester decomposition usually requires strict conditions, such as anhydrous solvent, careful degassing, and syringe pump addition, to avoid side reactions (including water addition, oxidation, and dimerization).
    • The typical metal-catalyzed α-diazoester decomposition usually requires strict conditions, such as anhydrous solvent, careful degassing, and syringe pump addition, to avoid side reactions (including water addition, oxidation, and dimerization).
  • 71
    • 53049091331 scopus 로고    scopus 로고
    • 1,n-enyne cycloisomerization reactions, the proposed gold-carbenoid could be intercepted by a carbon nucleophile.
    • In 1,n-enyne cycloisomerization reactions, the proposed gold-carbenoid could be intercepted by a carbon nucleophile:, C. H. M. Amijs, V. Lõpez-Carrillo, M. Raducan, P. Pérez-Galán, C. Ferrer, A. M. Echavarren, J. Org. Chem. 2008, 73, 7721.
    • (2008) J. Org. Chem. , vol.73 , pp. 7721
    • Amijs, C.H.M.1    Lõpez-Carrillo, V.2    Raducan, M.3    Pérez-Galán, P.4    Ferrer, C.5    Echavarren, A.M.6
  • 72
    • 84906949983 scopus 로고    scopus 로고
    • See Ref. [12] and [13].
    • See Ref. [12] and [13].
  • 76
    • 84906949984 scopus 로고    scopus 로고
    • See Ref. [11f] and [11c].
    • See Ref. [11f] and [11c].
  • 81
    • 84906949985 scopus 로고    scopus 로고
    • Ref. [25b]
    • Ref. [25b]
  • 83
    • 69249202400 scopus 로고    scopus 로고
    • For a theoretical study on ligand effects in gold-carbenoid chemistry, see.
    • For a theoretical study on ligand effects in gold-carbenoid chemistry, see:, D. Benitez, N. D. Shapiro, E. Tkatchouk, Y. Wang, W. A. Goddard III, F. D. Toste, Nat. Chem. 2009, 1, 482.
    • (2009) Nat. Chem. , vol.1 , pp. 482
    • Benitez, D.1    Shapiro, N.D.2    Tkatchouk, E.3    Wang III, Y.4    Toste, F.D.5
  • 88
    • 84906949986 scopus 로고    scopus 로고
    • Calculation results obtained with other DFT methods are summarized in the Supporting Information.
    • Calculation results obtained with other DFT methods are summarized in the Supporting Information.
  • 89
    • 84906949987 scopus 로고    scopus 로고
    • It is not clear at this moment whether this 1,2-proton shift is concerted or stepwise.
    • It is not clear at this moment whether this 1,2-proton shift is concerted or stepwise.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.