Highly efficient copper-catalyzed nitro-mannich type reaction:: Cross-dehydrogenative-coupling between sp3 C-H bond and sp3 C-H bond

被引:517
作者
Li, ZP [1 ]
Li, CJ [1 ]
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
关键词
D O I
10.1021/ja050058j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel C-C bond formation method was developed via the cross-dehydrogenative-coupling (CDC) reaction catalyzed by using copper bromide in the presence of an oxidizing reagent, tert-BuOOH. The CDC reaction provides a simple and efficient catalytic method to construct β-nitroamine via the reaction between sp3 C-H and sp3 C-H bonds. Copyright © 2005 American Chemical Society.
引用
收藏
页码:3672 / 3673
页数:2
相关论文
共 36 条
  • [1] The nitro-Mannich reaction and its application to the stereoselective synthesis of 1,2-diamines
    Adams, H
    Anderson, JC
    Peace, S
    Pennell, AMK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) : 9932 - 9934
  • [2] SELECTIVE INTERMOLECULAR CARBON-HYDROGEN BOND ACTIVATION BY SYNTHETIC METAL-COMPLEXES IN HOMOGENEOUS SOLUTION
    ARNDTSEN, BA
    BERGMAN, RG
    MOBLEY, TA
    PETERSON, TH
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (03) : 154 - 162
  • [3] Baer H. H., 1970, CHEM NITRO NITROSO 2, P117
  • [4] Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction)
    Ballini, R
    Petrini, M
    [J]. TETRAHEDRON, 2004, 60 (05) : 1017 - 1047
  • [5] Organocatalyzed solvent-free aza-Henry reaction:: A breakthrough in the one-pot synthesis of 1,2-diamines
    Bernardi, L
    Bonini, BF
    Capitò, E
    Dessole, G
    Comes-Franchini, M
    Fochi, M
    Ricci, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) : 8168 - 8171
  • [6] MAKING MERCURY-PHOTOSENSITIZED DEHYDRODIMERIZATION INTO AN ORGANIC SYNTHETIC METHOD - VAPOR-PRESSURE SELECTIVITY AND THE BEHAVIOR OF FUNCTIONALIZED SUBSTRATES
    BROWN, SH
    CRABTREE, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) : 2935 - 2946
  • [7] Copper-catalyzed enantioselective Henry reactions of α-keto esters:: An easy entry to optically active β-nitro-α-hydroxy esters and β-amino-α-hydroxy esters
    Christensen, C
    Juhl, K
    Hazell, RG
    Jorgensen, KA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) : 4875 - 4881
  • [8] Organometallic alkane CH activation
    Crabtree, RH
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (24) : 4083 - 4091
  • [9] Cross-coupling of sp3 C-H bonds and alkenes:: Catalytic cyclization of alkene-amide substrates
    DeBoef, B
    Pastine, SJ
    Sames, D
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (21) : 6556 - 6557
  • [10] Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222