Synthesis of Tertiary Enamides by Ag2CO3-Promoted Pd-Catalyzed Alkenylation of Acyclic Secondary Amides

被引：18

作者：

Delforge, Arnaud ^{[1
,2
]}

Georgiou, Irene ^{[1
,2
]}

Kremer, Adrian ^{[1
,2
]}

Wouters, Johan ^{[1
,2
]}

Bonifazi, Davide ^{[1
,2
,3
]}

机构：

[1] Univ Namur, Namur Res Coll, Rue Bruxelles 61, B-5000 Namur, Belgium

[2] Univ Namur, Dept Chem, Rue Bruxelles 61, B-5000 Namur, Belgium

[3] Cardiff Univ, Sch Chem, Pk Pl,Main Bldg, Cardiff CF10 3AT, S Glam, Wales

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 19期

关键词：

CROSS-COUPLING REACTIONS; C-N; ORGANIC-SYNTHESIS; NATURAL-PRODUCTS; VINYL HALIDES; COPPER; DERIVATIVES; PALLADIUM;

D O I：

10.1021/acs.orglett.6b02305

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Pd-catalyzed methodology for the preparation of tertiary enamides from acyclic secondary amides and bromo acrylates under mild reaction conditions has been developed using [Pd-2(dba)(3)], XantPhos, and Ag2CO3 as a base. The reaction occurs through a stereospecific metal-mediated oxidative-insertion mechanism.

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收藏

页码：4844 / 4847

页数：4

相关论文

共 39 条

[11] Stereoselective synthesis of enamides by a Peterson reaction manifold [J].

Furstner, A ;

Brehm, C ;

Cancho-Grande, Y .

ORGANIC LETTERS, 2001, 3 (24) :3955-3957

[12] Copper-mediated synthesis of N-acyl vinylogous carbamic acids and derivatives:: Synthesis of the antibiotic CJ-15,801 [J].

Han, C ;

Shen, RC ;

Su, S ;

Porco, JA .

ORGANIC LETTERS, 2004, 6 (01) :27-30

[13] Pd-Catalyzed N-Arylation of Secondary Acyclic Amides: Catalyst Development, Scope, and Computational Study [J].

Hicks, Jacqueline D. ;

Hyde, Alan M. ;

Cuezva, Alberto Martinez ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (46) :16720-16734

[14] Copper-catalyzed coupling of amides and carbamates with vinyl halides [J].

Jiang, L ;

Job, GE ;

Klapars, A ;

Buchwald, SL .

ORGANIC LETTERS, 2003, 5 (20) :3667-3669

[15] RUTHENIUM COMPLEX-CATALYZED ADDITION OF N-ARYL SUBSTITUTED AMIDES TO ALKYNES - NOVEL SYNTHESIS OF ENAMIDES [J].

KONDO, T ;

TANAKA, A ;

KOTACHI, S ;

WATANABE, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (04) :413-414

[16] Synthesis of 3-alkoxycarbonyl-1β-methylcarbapenem by using the palladium-catalyzed C-N bond-forming reaction between vinyl halide and β-lactam nitrogen [J].

Kozawa, Y ;

Mori, M .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (08) :3064-3067

[17]

Kuramochi K., 2000, SYNLETT, V2000, P397

[18] Cu-mediated enamide formation in the total synthesis of complex peptide natural products [J].

Kuranaga, Takefumi ;

Sesoko, Yusuke ;

Inoue, Masayuki .

NATURAL PRODUCT REPORTS, 2014, 31 (04) :514-532

[19] Novel ynamide structural analogues and their synthetic transformations [J].

Lu, Ting ;

Hsung, Richard P. .

ARKIVOC, 2014, :127-141

[20] Catalytic C-C, C-N, and C-O Ullmann-Type Coupling Reactions [J].

Monnier, Florian ;

Taillefer, Marc .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (38) :6954-6971

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