Hydroxylamine O-benzyl ether as an ammonia equivalent in the catalytic amination of aryl halides

被引:11
作者
Bedford, Robin B. [1 ]
Betham, Michael [1 ]
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/j.tetlet.2007.10.115
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium catalysed amination of aryl bromides with hydroxylamine O-benzyl ether leads to the formation of diaryl or triarylamines depending on the size of the aryl bromide, the number of equivalents used or the conditions employed. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8947 / 8950
页数:4
相关论文
共 19 条
[1]   Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles [J].
Anderson, Kevin W. ;
Tundel, Rachel E. ;
Ikawa, Takashi ;
Altman, Ryan A. ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6523-6527
[2]   N-trialkylsilylimines as coupling partners for Pd-catalyzed C-N bond-forming reactions:: One-step synthesis of imines and azadienes from aryl and alkenyl bromides [J].
Barluenga, J ;
Aznar, F ;
Valdés, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (03) :343-345
[3]   An evaluation of phosphine and carbene adducts of phosphiteand phosphinite-based palladacycles in the coupling of alkyl bromides with aryl boronic acids [J].
Bedford, RB ;
Betham, M ;
Coles, SJ ;
Frost, RM .
TETRAHEDRON, 2005, 61 (41) :9663-9669
[4]   N-Heterocyclic carbene adducts of orthopalladated triarylphosphite complexes [J].
Bedford, RB ;
Betham, M ;
Blake, ME ;
Frost, RM ;
Horton, PN ;
Hursthouse, MB ;
López-Nicolás, RM .
DALTON TRANSACTIONS, 2005, (16) :2774-2779
[5]   Equilibrium acidities and homolytic bond dissociation energies of N-H and/or O-H bonds in N-phenylhydroxylamine and its derivatives [J].
Bordwell, FG ;
Liu, WZ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (37) :8777-8781
[6]   New ammonia equivalents for the Pd-catalyzed amination of aryl halides [J].
Huang, XH ;
Buchwald, SL .
ORGANIC LETTERS, 2001, 3 (21) :3417-3419
[7]   Allyl amines as ammonia equivalents in the preparation of anilines and heteroarylamines [J].
Jaime-Figueroa, S ;
Liu, YZ ;
Muchowski, JM ;
Putman, DG .
TETRAHEDRON LETTERS, 1998, 39 (11) :1313-1316
[8]   Zinc trimethylsilylamide as a mild ammonia equivalent and base for the amination of aryl halides and triflates [J].
Lee, DY ;
Hartwig, JF .
ORGANIC LETTERS, 2005, 7 (06) :1169-1172
[9]   Palladium-catalyzed synthesis of arylamines from aryl halides and lithium bis(trimethylsilyl)amide as an ammonia equivalent [J].
Lee, S ;
Jorgensen, M ;
Hartwig, JF .
ORGANIC LETTERS, 2001, 3 (17) :2729-2732
[10]   Discrete high molecular weight triarylamine dendrimers prepared by palladium-catalyzed amination [J].
Louie, J ;
Hartwig, JF ;
Fry, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (48) :11695-11696