Copper-catalyzed coupling of amides and carbamates with vinyl halides

被引：395

作者：

Jiang, L ^{[1
]}

Job, GE ^{[1
]}

Klapars, A ^{[1
]}

Buchwald, SL ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 20期

关键词：

D O I：

10.1021/ol035355c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and efficient copper-catalyzed method for the amidation of vinyl bromides and iodides has been developed. This protocol uses a combination of 5 mol % copper iodide and 20 mol % N,N'-dimethyl ethylenediamine. Substrates bearing ester, silyl ether, and amino groups were successfully coupled under the reaction conditions. The double bond geometry of the vinyl halides was retained under the reaction conditions.

引用

收藏

页码：3667 / 3669

页数：3

相关论文

共 34 条

[1] Novel method for the synthesis of enamines by palladium catalyzed amination of alkenyl bromides [J].

Barluenga, J ;

Fernández, MA ;

Aznar, F ;

Valdés, C .

CHEMICAL COMMUNICATIONS, 2002, (20) :2362-2363

[2] SYNTHETIC STUDIES OF THE CYCLOPROPYL IMINIUM ION REARRANGEMENT .3. APPLICATION OF THE CYCLOPROPYL ACYLIMINIUM ION REARRANGEMENT TO A CONCISE AND HIGHLY CONVERGENT SYNTHESIS OF (+/-)-LYCORINE [J].

BOECKMAN, RK ;

GOLDSTEIN, SW ;

WALTERS, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (24) :8250-8252

[3] An efficient diamine copper complex-catalyzed coupling of arylboronic acids with imidazoles [J].

Collman, JP ;

Zhong, M .

ORGANIC LETTERS, 2000, 2 (09) :1233-1236

[4] ALPHA',ALPHA'-DISILYLATED TERTIARY BENZAMIDES AS DUAL ORTHO-CARBANION AND ALPHA'-CARBANION SYNTHONS - AMIDE PETERSON OLEFINATION ROUTES TO N-BENZOYL ENAMINES, ISOQUINOLINES, AND DIBENZAZOCINES [J].

CUEVAS, JC ;

PATIL, P ;

SNIECKUS, V .

TETRAHEDRON LETTERS, 1989, 30 (43) :5841-5844

[5] Novel lactone compounds from Mortierella verticillata that induce the human low density lipoprotein receptor gene:: Fermentation, isolation, structural elucidation and biological activities [J].

Dekker, KA ;

Aiello, RJ ;

Hirai, H ;

Inagaki, T ;

Sakakibara, T ;

Suzuki, Y ;

Thompson, JF ;

Yamauchi, Y ;

Kojima, N .

JOURNAL OF ANTIBIOTICS, 1998, 51 (01) :14-20

[6] Salicylihalamides A and B, novel cytotoxic macrolides from the marine sponge Haliclona sp. [J].

Erickson, KL ;

Beutler, JA ;

Cardellina, JH ;

Boyd, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8188-8192

[7]

Fürstner A, 2001, CHEM-EUR J, V7, P5286, DOI 10.1002/1521-3765(20011217)7:24<5286::AID-CHEM5286>3.0.CO

[8]

2-G

[9] Lobatamides A and B, novel cytotoxic macrolides from the tunicate Aplidium lobatum [J].

Galinis, DL ;

McKee, TC ;

Pannell, LK ;

Cardellina, JH ;

Boyd, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :8968-8969

[10] Formation of aryl-nitrogen, aryl-oxygen, and aryl-carbon bonds using well-defined copper(I)-based catalysts [J].

Gujadhur, RK ;

Bates, CG ;

Venkataraman, D .

ORGANIC LETTERS, 2001, 3 (26) :4315-4317

← 1 2 3 4 →