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 [J].

Beletskaya, IP ;

Cheprakov, AV .

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 [J].

Berman, AM ;

Johnson, JS .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :219-224

[3] Nickel-catalyzed electrophilic amination of organozinc halides [J].

Berman, AM ;

Johnson, JS .

SYNLETT, 2005, (11) :1799-1801

[4] Copper-catalyzed electrophilic amination of functionalized diarylzinc reagents [J].

Berman, AM ;

Johnson, JS .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :364-366

[5] Copper-catalyzed electrophilic amination of diorganozinc reagents [J].

Berman, AM ;

Johnson, JS .

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 [J].

Bernardi, P ;

Dembech, P ;

Fabbri, G ;

Ricci, A ;

Seconi, G .

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 [J].

Campbell, Matthew J. ;

Johnson, Jeffrey S. .

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 [J].

ERDIK, E ;

AY, M .

CHEMICAL REVIEWS, 1989, 89 (08) :1947-1980

← 1 2 3 4 →