Copper-catalyzed electrophilic amination of functionalized diarylzinc reagents

被引:80
作者
Berman, AM [1 ]
Johnson, JS [1 ]
机构
[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
关键词
D O I
10.1021/jo048168g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The copper-catalyzed electrophilic amination of functionalized diarylzinc reagents with O-acyl hydroxylamines allows for the preparation of functionalized tertiary arylamines in high yields, and is noteworthy for the mild reaction conditions employed. The functionalized diarylzinc reagents were prepared via an iodine/magnesium exchange of the corresponding aryl iodide followed by transmetalation of the resultant Grignard species with ZnCl2.
引用
收藏
页码:364 / 366
页数:3
相关论文
共 24 条
[11]   EFFECT OF COPPER(I) IODIDE AND MAGNESIUM-CHLORIDE ON AMINATION OF ARYL GRIGNARDS WITH KETOXIMES [J].
ERDIK, E ;
AY, M .
SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY, 1989, 19 (07) :663-668
[12]   ELECTROPHILIC AMINATION OF CARBANIONS [J].
ERDIK, E ;
AY, M .
CHEMICAL REVIEWS, 1989, 89 (08) :1947-1980
[13]  
Greck C, 1997, SYNLETT, P741
[14]   Carbon-heteroatom bond-forming reductive eliminations of amines, ethers, and sulfides [J].
Hartwig, JF .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (12) :852-860
[15]   Copper-catalyzed halogen exchange in aryl halides: An aromatic Finkelstein reaction [J].
Klapars, A ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) :14844-14845
[16]   Highly functionalized organomagnesium reagents prepared through halogen-metal exchange [J].
Knochel, P ;
Dohle, W ;
Gommermann, N ;
Kneisel, FF ;
Kopp, F ;
Korn, T ;
Sapountzis, I ;
Vu, VA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (36) :4302-4320
[17]   Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation [J].
Ley, SV ;
Thomas, AW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) :5400-5449
[18]   Practical palladium catalysts for C-N and C-O bond formation [J].
Muci, AR ;
Buchwald, SL .
CROSS-COUPLING REACTIONS: A PRACTICAL GUIDE, 2002, 219 :131-209
[19]   A general amination method based on the addition of polyfunctional arylmagnesium reagents to functionalized arylazo tosylates [J].
Sapountzis, I ;
Knochel, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (07) :897-900
[20]   A new general preparation of polyfunctional diarylamines by the addition of functionalized arylmagnesium compounds to nitroarenes [J].
Sapountzis, I ;
Knochel, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (32) :9390-9391