Copper-promoted N-cyclopropylation of anilines and amines by cyclopropylboronic acid

被引:49
作者
Benard, Sebastien [1 ]
Neuville, Luc [1 ]
Zhu, Jieping [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France
关键词
CROSS-COUPLING REACTIONS; ARYLBORONIC ACIDS; C-N; CUPROUS CHLORIDE; BOND FORMATION; BIS(MU-OXO)DICOPPER COMPLEXES; CUPRIC ACETATE; CYCLIC AMIDES; MECHANISM; OXIDATION;
D O I
10.1039/b925499d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reaction of anilines, primary and secondary aliphatic amines with cyclopropylboronic acid in dichloroethane in the presence of Cu(OAc)(2) (1 equiv.), 2,2'-bipyridine (1 equiv.) and sodium carbonate or sodium bicarbonate (2 equiv.) under air atmosphere afforded the corresponding N-cyclopropyl derivatives in good to excellent yields.
引用
收藏
页码:3393 / 3395
页数:3
相关论文
共 34 条
  • [1] Copper-catalyzed coupling of arylboronic acids and amines
    Antilla, JC
    Buchwald, SL
    [J]. ORGANIC LETTERS, 2001, 3 (13) : 2077 - 2079
  • [2] Copper in cross-coupling reactions - The post-Ullmann chemistry
    Beletskaya, IP
    Cheprakov, AV
    [J]. COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) : 2337 - 2364
  • [3] Copper-mediated N-cyclopropylation of azoles, amides, and sulfonamides by cyclopropylboronic acid
    Benard, Sebastien
    Neuville, Luc
    Zhu, Jieping
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (16) : 6441 - 6444
  • [4] Cytochrome P450-catalyzed oxidation of N-benzyl-N-cyclopropylamine generates both cyclopropanone hydrate and 3-hydroxypropionaldehyde via hydrogen abstraction, not single electron transfer
    Cerny, MA
    Hanzlik, RP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (10) : 3346 - 3354
  • [5] New N- and O-arylations with phenylboronic acids and cupric acetate
    Chan, DMT
    Monaco, KL
    Wang, RP
    Winters, MP
    [J]. TETRAHEDRON LETTERS, 1998, 39 (19) : 2933 - 2936
  • [6] Chan DMT, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, P205, DOI 10.1002/3527606548.ch5
  • [7] The [Cu(OH)•TMEDA]2Cl2-catalyzed coupling of arylboronic acids with imidazoles in water
    Collman, JP
    Zhong, M
    Zeng, L
    Costanzo, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) : 1528 - 1531
  • [8] An efficient diamine copper complex-catalyzed coupling of arylboronic acids with imidazoles
    Collman, JP
    Zhong, M
    [J]. ORGANIC LETTERS, 2000, 2 (09) : 1233 - 1236
  • [9] The synthesis of N-arylcyclopropylamines via palladium-catalyzed C-N bond formation
    Cui, W
    Loeppky, RN
    [J]. TETRAHEDRON, 2001, 57 (15) : 2953 - 2956
  • [10] Direct N-cyclopropylation of cyclic amides and azoles employing a cyclopropylbismuth reagent
    Gagnon, Alexandre
    St-Onge, Miguel
    Little, Kelly
    Duplessis, Martin
    Barabe, Francis
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (01) : 44 - 45