Addition of boranes to N-aryl-salicylaldimines: Intramolecular hydrogenation of imines

被引：7
作者：
Barnes, Stephanie S. [1 ]
Vogels, Christopher M. [1 ]
Decken, Andreas [2 ]
Westcott, Stephen A. [1 ]
机构：
[1] Mt Allison Univ, Dept Chem & Biochem, Sackville, NB E4L 1G8, Canada
[2] Univ New Brunswick, Dept Chem, Fredericton, NB E3B 5A3, Canada
来源：
DALTON TRANSACTIONS | 2011年 / 40卷 / 17期
基金：
加拿大自然科学与工程研究理事会;
关键词：
FRUSTRATED LEWIS PAIRS; METAL-CATALYZED HYDROBORATION; CRYSTAL-STRUCTURE; STEREOSELECTIVE ADDITION; BOND-CLEAVAGE; C=N BOND; ACTIVATION; REACTIVITY; ACID; PHOSPHINES;
D O I：
10.1039/c1dt10132c
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Addition of boranes to N-aryl-salicylaldimines takes place initially at the reactive phenolic O-H bond to give an activated boron-containing imine and dihydrogen. In some cases a subsequent intramolecular hydrogenation step is observed and the C=N imine bond is reduced to the corresponding amine. Reactions with dimesitylborane in THF are unique in that the reduced amine product is the major product observed in solution.
引用
收藏
页码：4707 / 4714
页数：8
相关论文
共 107 条
  • [1] Synthesis and characterization of boronates derived from non-symmetric amino-bis-phenols
    Abreu, A
    Alas, SJ
    Beltrán, HI
    Santillan, R
    Farfán, N
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (03) : 337 - 348
  • [2] [Anonymous], SADABS 2008
  • [3] [Anonymous], 2006, SAINT 7 23A
  • [4] ARAUJO JC, 2002, J ORGANOMET CHEM, V646, P179
  • [5] Stereocontrolled Synthesis of Highly Functionalized Quaternary Carbon Centers: A Route to α-Substituted Serines
    Ariza, Xavier
    Cornella, Josep
    Font-Bardia, Merce
    Garcia, Jordi
    Ortiz, Jordi
    Sanchez, Carolina
    Solans, Xavier
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) : 4202 - 4205
  • [6] Structure and Dynamic Features of an Intramolecular Frustrated Lewis Pair
    Axenov, Kirill V.
    Moemming, Cornelia M.
    Kehr, Gerald
    Froehlich, Roland
    Erker, Gerhard
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (47) : 14069 - 14073
  • [7] COINAGE METAL-CATALYZED HYDROBORATION OF IMINES
    BAKER, RT
    CALABRESE, JC
    WESTCOTT, SA
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 498 (02) : 109 - 117
  • [8] Boron-nitrogen macrocycles:: a new generation of calix[3]arenes
    Barba, V
    Höpfl, H
    Farfán, N
    Santillan, R
    Beltran, HI
    Zamudio-Rivera, LS
    [J]. CHEMICAL COMMUNICATIONS, 2004, (24) : 2834 - 2835
  • [9] Stereoselective addition of acetone to the C=N bond of [4.3.0] boron heterobicycles
    Barba, V
    Cuahutle, D
    Santillan, R
    Farfán, N
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2001, 79 (08): : 1229 - 1237
  • [10] 3-Aminophenylboronic acid as building block for the construction of calix- and cage-shaped boron complexes
    Barba, Victor
    Hernandez, Refugio
    Hopfl, Herbert
    Santillan, Rosa
    Farfan, Norberto
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (14) : 2127 - 2133
12345678910