Nickel-catalyzed 1,2-addition of arylboroxines to aromatic aldehydes

被引：61
作者：
Arao, Takafumi [1 ]
Kondo, Kazuhiro [1 ]
Aoyama, Toyohiko [1 ]
机构：
[1] Nagoya City Univ, Grad Sch Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 23期
关键词：
nickel; arylation; 1,2-addition; boroxine; aldehyde; Duphos;
D O I：
10.1016/j.tetlet.2007.04.025
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Development of Ni-Et-Duphos-catalyzed 1,2-addition of arylboroxines to aromatic aldehydes is described. The dramatic effect of boron reagent and phosphine ligand is observed. This method with a phosphine ligand allows asymmetric arylation of aromatic aldehydes (up to 78% ee). (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4115 / 4117
页数：3
相关论文
共 24 条
  • [1] Function of an N-heterocyclic carbene ligand based on concept of chiral mimetic
    Arao, Takafumi
    Sato, Kei
    Kondo, Kazuhiro
    Aoyama, Toyohiko
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (11) : 1576 - 1581
  • [2] Asymmetric synthesis of diarylmethanols: Development of a hemilabile phosphorus ligand based on the concept of conformational control
    Arao, Takafumi
    Suzuki, Kiyoto
    Kondo, Kazuhiro
    Aoyama, Toyobiko
    [J]. SYNTHESIS-STUTTGART, 2006, (22): : 3809 - 3814
  • [3] Catalyzed asymmetric aryl transfer reactions to aldehydes with boronic acids as aryl source
    Bolm, C
    Rudolph, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) : 14850 - 14851
  • [4] Planar chiral imidazolium salts in the asymmetric rhodium-catalyzed 1,2-addition of arylboronic acids to aldehydes
    Focken, T
    Rudolph, J
    Bolm, C
    [J]. SYNTHESIS-STUTTGART, 2005, (03): : 429 - 436
  • [5] Fürstner A, 2001, ADV SYNTH CATAL, V343, P343
  • [6] Nickel-catalyzed alkylation of aldehydes with trialkylboranes
    Hirano, K
    Yorimitsu, H
    Oshima, K
    [J]. ORGANIC LETTERS, 2005, 7 (21) : 4689 - 4691
  • [7] Ligand-dependent scope and divergent mechanistic behavior in nickel-catalyzed reductive couplings of aldehydes and alkynes
    Mahandru, GM
    Liu, G
    Montgomery, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) : 3698 - 3699
  • [8] Catalytic asymmetric reductive coupling of alkynes and aldehydes:: Enantioselective synthesis of allylic alcohols and α-hydroxy ketones
    Miller, KM
    Huang, WS
    Jamison, TF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (12) : 3442 - 3443
  • [9] Rhodium-catalysed aryl transfer to aldehydes: counterion effects with nitrogen containing ligands
    Moreau, C
    Hague, C
    Weller, AS
    Frost, CG
    [J]. TETRAHEDRON LETTERS, 2001, 42 (39) : 6957 - 6960
  • [10] Direct observation of oxidative Cyclization of η2-alkene and η2-aldehyde on Ni(0) center.: Significant acceleration by addition of Me3SiOTf
    Ogoshi, S
    Oka, M
    Kurosawa, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (38) : 11802 - 11803
123