N-alkyl-2-pyridylmethanimines as tuneable alternatives to bipyridine ligands in copper mediated atom transfer radical cyclisation.

被引:44
作者
Clark, AJ [1 ]
Duncalf, DJ
Filik, RP
Haddleton, DM
Thomas, GH
Wongtap, H
机构
[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England
[2] Knoll Pharmaceut, Dept Res & Dev, Nottingham NG1 1GF, England
关键词
radicals; addition; copper; lactam;
D O I
10.1016/S0040-4039(99)00533-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper halide complexes of N-alkyl-2-pyridylmethanimines (3, 11-14) catalyse atom transfer radical cyclisation reactions of activated (6a-b) and unactivated alpha-haloallylacetamides (9) at room temperature. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3807 / 3810
页数:4
相关论文
共 19 条
  • [1] 3-oxa- and 3-azabicyclo[3.1.0]hexan-2-ones via tandem radical cyclization-intramolecular S(N)2 reactions
    Baldovini, N
    Bertrand, MP
    Carriere, A
    Nouguier, R
    Plancher, JM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) : 3205 - 3208
  • [2] CLARK AJ, 1997, J CHEM SOC CHEM COMM, P1734
  • [3] DECAMPO F, 1999, J CHEM SOC CHEM COMM, P2117
  • [4] Halogen atom transfer radical addition of alpha-polychloroesters to olefins promoted by Fe-0 filings
    Forti, L
    Ghelfi, F
    Libertini, E
    Pagnoni, UM
    Soragni, E
    [J]. TETRAHEDRON, 1997, 53 (52) : 17761 - 17768
  • [5] Fe-0 initiated halogen atom transfer radical addition of methyl 2-Br-2-Cl-carboxylates to olefins
    Forti, L
    Ghelfi, F
    Pagnoni, UM
    [J]. TETRAHEDRON LETTERS, 1996, 37 (12) : 2077 - 2078
  • [6] Atom transfer polymerisation of methyl methacrylate: use of chiral aryl/alkyl pyridylmethanimine ligands; with copper(I) bromide and as structurally characterised chiral copper(I) complexes
    Haddleton, DM
    Duncalf, DJ
    Kukulj, D
    Heming, AM
    Shooter, AJ
    Clark, AJ
    [J]. JOURNAL OF MATERIALS CHEMISTRY, 1998, 8 (07) : 1525 - 1532
  • [7] Copper diimine complexes:: the synthesis and crystal structures of [Cu(C10H14N2)2(MeOH)][BF4], [Cu(C10H20N2)2]Br, [{(C10H14N2)CuBr(μ-OMe)}2(MeOH)] and [{(C10H20N2)CuBr(μ-OMe)}2]
    Haddleton, DM
    Clark, AJ
    Duncalf, DJ
    Heming, AM
    Kukulj, D
    Shooter, AJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1998, (03): : 381 - 385
  • [8] Haddleton DM, 1998, EUR J INORG CHEM, P1799
  • [9] Atom transfer polymerisation of methyl methacrylate mediated by solid supported copper catalysts
    Haddleton, DM
    Kukulj, D
    Radigue, AP
    [J]. CHEMICAL COMMUNICATIONS, 1999, (01) : 99 - 100
  • [10] First structurally authenticated inorganic polymers of CuBr and CuI containing chiral bidentate N-donor ligands.: Use of the Schiff base 2,2′-bis[(4S)-4-benzyl-2-oxazoline] as ligand
    Haddleton, DM
    Duncalf, DJ
    Clark, AJ
    Crossman, MC
    Kukulj, D
    [J]. NEW JOURNAL OF CHEMISTRY, 1998, 22 (04) : 315 - 317