Palladium-catalyzed intermolecular ene-yne coupling: Development of an atom-efficient Mizoroki-Heck-type reaction

被引：79

作者：

Lindhardt , Anders T. ^{[1
,2
]}

Mantel, Mette Louise H. ^{[1
,2
]}

Skrydstrup, Troels ^{[1
,2
]}

机构：

[1] Univ Aarhus, Ctr Insoluble Prot Struct inSPIN, Dept Chem, Aarhus 8000, Denmark

[2] Univ Aarhus, Interdisciplinary Nanosci Ctr, Aarhus 8000, Denmark

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 14期

关键词：

alkenes; alkynes; Mizoroki-Heck reaction; palladium; phosphane ligands;

D O I：

10.1002/anie.200705558

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Direct and to the point: A palladium(II) catalytic system based on a palladium hydride species provides access to highly substituted 1,3-dienes through a direct coupling of alkynes with alkenes in a base-free Mizoroki-Heck-type reaction with full atom economy (see scheme; R=amide, borate, C(OH)Me2, O-alkyl). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

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页码：2668 / 2672

页数：5

相关论文

共 42 条

[1] Palladium(0) alkyne complexes as active species: a DFT investigation [J].

Ahlquist, M ;

Fabrizi, G ;

Cacchi, S ;

Norrby, PO .

CHEMICAL COMMUNICATIONS, 2005, (33) :4196-4198

[2] The mechanism of the phosphine-free palladium-catalyzed hydroarylation of alkynes [J].

Ahlquist, Marten ;

Fabrizi, Giancarlo ;

Cacchi, Sandro ;

Norrby, Per-Ola .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12785-12793

[3] Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 1: The Heck reaction [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

TETRAHEDRON, 2005, 61 (50) :11771-11835

[4] The behavior of 1,n-enynes in the presence of transition metals [J].

Aubert, C ;

Buisine, O ;

Malacria, M .

CHEMICAL REVIEWS, 2002, 102 (03) :813-834

[5] Synthesis of cyclic peptides using a palladium-catalyzed enyne cycloisomerization [J].

Balraju, V. ;

Dev, R. Vasu ;

Reddy, D. Srinivasa ;

Iqbal, Javed .

TETRAHEDRON LETTERS, 2006, 47 (21) :3569-3571

[6] Selected patented cross-coupling reaction technologies [J].

Corbet, Jean-Pierre ;

Mignani, Gerard .

CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710

[7]

DEMEIJERE A, METALCATALYZED CROSS

[8] Synthesis of 2-alkoxy-5-methylenetetrahydropyrans: A regioselective ruthenium-catalyzed C-C coupling reaction of prop-2-yn-1-ols with allyl alcohol [J].

Derien, S ;

Ropartz, L ;

Le Paih, J ;

Dixneuf, PH .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3524-3531

[9] Studies on the heck reaction with alkenyl phosphates: Can the 1,2-migration be controlled? Scope and limitations [J].

Ebran, Jean-Philippe ;

Hansen, Anders L. ;

Gogsig, Thomas M. ;

Skrydstrup, Troels .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (21) :6931-6942

[10] Hydride complexes of palladium [J].

Grushin, VV .

CHEMICAL REVIEWS, 1996, 96 (06) :2011-2033

← 1 2 3 4 5 →