Umpolung Amination: Nickel-Catalyzed Coupling Reactions of N,N-Dialkyl-N-chloroamines with Diorganozinc Reagents

被引：151

作者：

Barker, Timothy J. ^{[1
]}

Jarvo, Elizabeth R. ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 43期

关键词：

ELECTROPHILIC AMINATION; REDUCTIVE ELIMINATION; COPPER; REACTIVITY; HALIDES;

D O I：

10.1021/ja907038b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N,N-Dialkyl-N-chloroamines are an effective source of electrophilic nitrogen for nickel-catalyzed coupling with diarylzinc reagents. A variety of N-chloroamines as well as organozinc reagents react smoothly under the reaction conditions. A one-pot procedure that circumvents the need to isolate the N-chloroamines is described.

引用

页码：15598 / +

页数：3

共 32 条

[1] Copper in cross-coupling reactions - The post-Ullmann chemistry
Beletskaya, IP
Cheprakov, AV
[J]. COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) : 2337 - 2364
[2] Copper-catalyzed electrophilic amination of organozinc nucleophiles:: Documentation of O-benzoyl hydroxylamines as broadly useful R2N(+) and RHN(+) synthons
Berman, AM
Johnson, JS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) : 219 - 224
[3] Nickel-catalyzed electrophilic amination of organozinc halides
Berman, AM
Johnson, JS
[J]. SYNLETT, 2005, (11) : 1799 - 1801
[4] Copper-catalyzed electrophilic amination of functionalized diarylzinc reagents
Berman, AM
Johnson, JS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) : 364 - 366
[5] Copper-catalyzed electrophilic amination of diorganozinc reagents
Berman, AM
Johnson, JS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) : 5680 - 5681
[6] A general and convenient procedure for the synthesis of N-alkylarylamines and N-alkylheteroarylamines by electrophilic amination of cuprates with N-alkylhydroxylamines
Bernardi, P
Dembech, P
Fabbri, G
Ricci, A
Seconi, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (02) : 641 - 643
[7] Mechanistic studies of the copper-catalyzed electrophilic amination of diorganozinc reagents and development of a zinc-free protocol
Campbell, Matthew J.
Johnson, Jeffrey S.
[J]. ORGANIC LETTERS, 2007, 9 (08) : 1521 - 1524
[8] Dembech P, 2000, CHEM-EUR J, V6, P1281, DOI 10.1002/(SICI)1521-3765(20000417)6:8<1281::AID-CHEM1281>3.0.CO
[9] 2-F
[10] ELECTROPHILIC AMINATION OF CARBANIONS
ERDIK, E
AY, M
[J]. CHEMICAL REVIEWS, 1989, 89 (08) : 1947 - 1980

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