Metal-Free Transfer Hydrogenation Catalysis by B(C6F5)3

被引:91
|
作者
Farrell, Jeffrey M. [1 ]
Heiden, Zachariah M. [1 ]
Stephan, Douglas W. [1 ]
机构
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
DYNAMIC KINETIC RESOLUTION; CHIRAL AMINES; RACEMIZATION; IMINES; REDUCTION; PHOSPHINES; REACTIVITY; DIHYDROGEN; ACTIVATION; ALCOHOLS;
D O I
10.1021/om2005832
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The activation of amines by B(C6F5)(3) is shown to effect the catalytic racemization of a chiral amine. Extending this strategy to a bimolecular process, catalytic transfer hydrogenation of imines, enamines, and N-heterocycles is demonstrated using iPr(2)NH as the source of hydrogen and a catalytic amount of the Lewis acid B(C6F5)(3).
引用
收藏
页码:4497 / 4500
页数:4
相关论文
共 50 条
  • [21] Metal-free synthesis of 3,3′-bisindolylmethanes in water using Ph3C+[B(C6F5)4]- as the pre-catalyst
    Zhang, Zhenguo
    Ji, Liang
    Liu, Xiaoxiao
    Li, Zhihong
    Lv, Yongheng
    Jia, Zhenhua
    Loh, Teck-Peng
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (19): : 5154 - 5159
  • [22] Metal-free synthesis of 3,3′-bisindolylmethanes in water using Ph3C+[B(C6F5)4]− as the pre-catalyst
    Zhang, Zhenguo
    Ji, Liang
    Liu, Xiaoxiao
    Li, Zhihong
    Lv, Yongheng
    Jia, Zhenhua
    Loh, Teck-Peng
    Organic Chemistry Frontiers, 2022, 9 (19) : 5154 - 5159
  • [23] B(C6F5)3 adducts of transition metal acyl compounds
    Llewellyn, SA
    Green, MLH
    Cowley, AR
    DALTON TRANSACTIONS, 2006, (14) : 1776 - 1783
  • [24] Activation of constrained geometry dialkyl complexes with B(C6F5)3 and Al(C6F5)3.: New mode of metallocene activation by B(C6F5)3.
    Klosin, J
    Abboud, KA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U731 - U731
  • [25] Metal-Free Acetylene Coupling by the (C6F5)2B-X 1,2-Halogenoboration Reaction
    Ueno, Atsushi
    Li, Jun
    Daniliuc, Constantin G.
    Kehr, Gerald
    Erker, Gerhard
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (40) : 10044 - 10048
  • [26] B(C6F5)3 mediated arene hydrogenation/transannulation of para-methoxyanilines
    Longobardi, Lauren E.
    Mahdi, Tayseer
    Stephan, Douglas W.
    DALTON TRANSACTIONS, 2015, 44 (16) : 7114 - 7117
  • [27] B(C6F5)3 catalysis accelerates the hydrosilane chlorination by Ph3CCl
    Simarek, Adam
    Lamac, Martin
    Horacek, Michal
    Pinkas, Jiri
    APPLIED ORGANOMETALLIC CHEMISTRY, 2018, 32 (08)
  • [28] Photo Lewis acid generators: photorelease of B(C6F5)3 and applications to catalysis
    Khalimon, Andrey Y.
    Shaw, Bryan K.
    Marwitz, Adam J. V.
    Piers, Warren E.
    Blackwell, James M.
    Parvez, Masood
    DALTON TRANSACTIONS, 2015, 44 (41) : 18196 - 18206
  • [29] Heterolytic dihydrogen activation with the 1,8-bis(diphenylphosphino)-naphthalene/B(C6F5)3 pair and its application for metal-free catalytic hydrogenation of silyl enol ethers
    Wang, Huadong
    Froehlich, Roland
    Kehr, Gerald
    Erker, Gerhard
    CHEMICAL COMMUNICATIONS, 2008, (45) : 5966 - 5968
  • [30] Transition metal-free hydrodefluorination of acid fluorides and organofluorines by Ph3GeH promoted by catalytic [Ph3C][B(C6F5)4]
    Hayatifar, Ardalan
    Borrego, Alejandro
    Bosek, David
    Czarnecki, Matthew
    Derocher, Gabriel
    Kuplicki, Adam
    Lytle, Erik
    Padilla, Jonas
    Paroly, Charles
    Tubay, Gillian
    Vyletel, Jackson
    Weinert, Charles S.
    CHEMICAL COMMUNICATIONS, 2019, 55 (73) : 10852 - 10855