N-amidation by copper-mediated cross-coupling of organostannanes or boronic acids with O-acetyl hydroxamic acids

被引：124

作者：

Zhang, Zhihui ^{[1
]}

Yu, Ying ^{[1
]}

Liebeskind, Lanny S. ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 14期

关键词：

D O I：

10.1021/ol8009682

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general nonoxidative N-amidation of organostannanes and boronic acids has been developed. Under nonbasic conditions a wide variety of aryl, alkenyl, and heteroaryl organostannanes and boronic acids couple efficiently with O-acetyl hydroxamic acids in the presence of Cu(I) sources.

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页码：3005 / 3008

页数：4

相关论文

共 40 条

[1] Copper-mediated cross-coupling of organostannanes with organic iodides at or below room temperature [J].

Allred, GD ;

Liebeskind, LS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (11) :2748-2749

[2] Copper-catalyzed coupling of arylboronic acids and amines [J].

Antilla, JC ;

Buchwald, SL .

ORGANIC LETTERS, 2001, 3 (13) :2077-2079

[3] Transition-metal-catalyzed reactions of carbon-heteroatom bond formation by substitution and addition processes [J].

Beletskaya, IP .

PURE AND APPLIED CHEMISTRY, 2005, 77 (12) :2021-2027

[4] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[5] 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

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

Berman, AM ;

Johnson, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) :5680-5681

[7] Enamide synthesis by copper-catalyzed cross-coupling of amides and potassium alkenyltrifluoroborate salts [J].

Bolshan, Yuri ;

Batey, Robert A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (11) :2109-2112

[8] Industrial-scale palladium-catalyzed coupling of aryl halides and amines - A personal account [J].

Buchwald, SL ;

Mauger, C ;

Mignani, G ;

Scholz, U .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) :23-39

[9] 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

[10] Copper promoted C-N and C-O bond cross-coupling with phenyl and pyridylboronates [J].

Chan, DMT ;

Monaco, KL ;

Li, RH ;

Bonne, D ;

Clark, CG ;

Lam, PYS .

TETRAHEDRON LETTERS, 2003, 44 (19) :3863-3865

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