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Volumn 352, Issue 13, 2010, Pages 2315-2320

An efficient and general microwave-assisted copper-catalyzed Conia-ene reaction of terminal and internal alkynes tethered to a wide variety of carbonucleophiles

Author keywords

Alkynes; Conia ene reaction; Copper; Cyclization; Microwave irradiation

Indexed keywords


EID: 77956917552     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000351     Document Type: Article
Times cited : (47)

References (61)
  • 20
    • 27644479913 scopus 로고    scopus 로고
    • Recatalyzed reactions: b Ni/Yb-catalyzed reactions
    • Recatalyzed reactions: b) Y. Kuninobu, A. Kawata, K. Takai, Org. Lett. 2005, 7, 4823; Ni/Yb-catalyzed reactions:
    • (2005) Org. Lett. , vol.7 , pp. 4823
    • Kuninobu, Y.1    Kawata, A.2    Takai, K.3
  • 28
    • 25444522675 scopus 로고    scopus 로고
    • Pd/Yb-catalyzed reactions
    • i) F. Gagosz, Org. Lett. 2005, 7, 4133; Pd/Yb-catalyzed reactions:
    • (2005) Org. Lett. , vol.7 , pp. 4133
    • Gagosz, F.1
  • 34
    • 0000541824 scopus 로고    scopus 로고
    • For other related metal-catalyzed cyclization reactions leading to nitrogen and oxygen heterocycles, see: a) X. Marat, N. Monteiro, G. Balme, Synlett 1997, 845;
    • (1997) Synlett , pp. 845
    • Marat, X.1    Monteiro, N.2    Balme, G.3
  • 44
    • 77956936369 scopus 로고    scopus 로고
    • All. In this Cu/Ag cocatalyzed Conia-ene reaction, 2-(pent-4-ynyl) malononitrile remained unaffected while 2-(pent-4-ynyl)malonate gave moderate yields of the corresponding cyclized product having the double bond in the endocyclic position
    • C.-L. Deng, T. Zou, Z.-Q. Wang, R.-J. Song, S.-M. Guo, J.-H. Li, J. Org. Chem. 2009, 74, All. In this Cu/Ag cocatalyzed Conia-ene reaction, 2-(pent-4-ynyl)malononitrile remained unaffected while 2-(pent-4-ynyl)malonate gave moderate yields of the corresponding cyclized product having the double bond in the endocyclic position.
    • (2009) J. Org. Chem. , pp. 74
    • Deng, C.-L.1    Zou, T.2    Wang, Z.-Q.3    Song, R.-J.4    Guo, S.-M.5    Li, J.-H.6
  • 45
    • 12344326692 scopus 로고    scopus 로고
    • for the use of this copper catalyst in coupling reactions see
    • This copper complex is commercially available or easily prepared using known procedures: a) C. G. Bates, P. Saejueng, M. Q. Doherty, D. Venkataraman, Org. Lett. 2004, 6, 5005 ; for the use of this copper catalyst in coupling reactions see:
    • (2004) Org. Lett. , vol.6 , pp. 5005
    • Bates, C.G.1    Saejueng, P.2    Doherty, M.Q.3    Venkataraman, D.4
  • 48
    • 18244368519 scopus 로고    scopus 로고
    • For recent reviews on microwave-assisted organic synthesis, see: a) C. O. Kappe, Angew. Chem. 2004, 116, 6408;
    • (2004) Angew. Chem. , vol.116 , pp. 6408
    • Kappe, C.O.1
  • 51
    • 33846895846 scopus 로고    scopus 로고
    • A. Loupy, (Ed. ), 2nd edn., Wiley-VCH, Weinheim
    • c) A. Loupy, (Ed. ), in: Microwaves in Organic Synthesis, 2nd edn., Wiley-VCH, Weinheim, 2006.
    • (2006) Microwaves in Organic Synthesis
  • 52
    • 0003512405 scopus 로고
    • Copper iodide can promote the cyclization of Ig, but stoichiometric quantities of copper salt, base and protonating species are needed, see: a) N. Monteiro, G. Balme, I Goré, Synlett 1992, 227;
    • (1992) Synlett , pp. 227
    • Monteiro, N.1    Balme, G.2    Goré, I.3
  • 56
    • 77956944657 scopus 로고    scopus 로고
    • [5h]
    • [5h]
  • 58
    • 34248345141 scopus 로고    scopus 로고
    • 2, 4a was obtained in only 55% along with 5% of the 6-endo decarboxylated product
    • 2, 4a was obtained in only 55% along with 5% of the 6-endo decarboxylated product.
    • (2007) Org. Lett. , vol.9 , pp. 1703
    • Yu, F.1    Lian, X.2    Ma, S.3
  • 59
    • 0025899436 scopus 로고
    • The stereochemistry of the exocyclic double bond in 4a was found to be E by comparison of its spectral and analytical data with those of the compound prepared from the reaction of la with methyl 4-iodobenzoate ac- cording to a procedure reported by us earlier
    • The stereochemistry of the exocyclic double bond in 4a was found to be E by comparison of its spectral and analytical data with those of the compound prepared from the reaction of la with methyl 4-iodobenzoate ac- cording to a procedure reported by us earlier: G. Fournet, G. Balme, I Goré, Tetrahedron 1991, 47, 6293.
    • (1991) Tetrahedron , vol.47 , pp. 6293
    • Fournet, G.1    Balme, G.2    Goré, I.3
  • 60
    • 77956937100 scopus 로고    scopus 로고
    • [5k] and references cited therein
    • [5k] and references cited therein.
  • 61


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