Copper(I)-mediated oxidative cross-coupling between functionalized alkynyl lithium and aryl magnesium reagents

被引：71

作者：

Dubbaka, Srinivas Reddy ^{[1
]}

Kienle, Marcel ^{[1
]}

Mayr, Herbert ^{[1
]}

Knochel, Paul ^{[1
]}

机构：

[1] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 47期

关键词：

alkynes; cross-coupling; cuprates; nitrogen heterocycles;

D O I：

10.1002/anie.200703097

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) All crossed: The reaction of unsaturated copper reagents with various alkynyl lithium compounds provides mixed lithium cuprates, which in the presence of chloranil undergo an oxidative coupling, thus leading to polyfunctional alkynes or enynes. Bromoenynes prepared by this method are readily converted into pyridine derivatives by a new ring closure that proceeds at low temperature (see scheme, tol = tolyl). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：9093 / 9096

页数：4

共 75 条

[21]

Fischer, 2007, ANGEW CHEM, V119, P4848

[22] Synthesis of 1,3,4-trisubstituted isoquinolines by iodine-mediated electrophilic cyclization of 2-alkynyl benzyl azides [J].

Fischer, Dirk ;

Tomeba, Hisamitsu ;

Pahadi, Nirmal K. ;

Patil, Nitin T. ;

Yamamoto, Yoshinori .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (25) :4764-4766

[23] Efficient palladium-catalyzed coupling of aryl chlorides and tosylates with terminal alkynes: Use of a copper cocatalyst inhibits the reaction [J].

Gelman, D ;

Buchwald, SL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (48) :5993-5996

[24]

Gelman D., 2003, ANGEW CHEM, V115, P6175, DOI 10.1002/ange.200353015

[25] Covalent assembly of molecular ladders [J].

Hartley, C. Scott ;

Elliott, Erin L. ;

Moore, Jeffrey S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (15) :4512-+

[26] Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].

Hassan, J ;

Sévignon, M ;

Gozzi, C ;

Schulz, E ;

Lemaire, M .

CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469

[27] Synthesis of isoquinolines and naphthyridines by electrophilic ring closure of iminoalkynes [J].

Huang, QH ;

Hunter, JA ;

Larock, RC .

ORGANIC LETTERS, 2001, 3 (19) :2973-2976

[28] Pd(PhCN)2Cl2/P(t-Bu)3:: A versatile catalyst for sonogashira reactions of aryl bromides at room temperature [J].

Hundertmark, T ;

Littke, AF ;

Buchwald, SL ;

Fu, GC .

ORGANIC LETTERS, 2000, 2 (12) :1729-1731

[29] Modern amination reactions [J].

Kienle, Marcel ;

Dubbaka, Srinivas Reddy ;

Brade, Katia ;

Knochel, Paul .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (25) :4166-4176

[30] Preparation of tertiary amines via the oxidative coupling of polyfunctional aryl and heteroaryl amidocuprates [J].

Kienle, Marcel ;

Dubbaka, Srinivas Reddy ;

del Amo, Vicente ;

Knochel, Paul .

SYNTHESIS-STUTTGART, 2007, (08) :1272-1278

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