The scope of the Heck arylation of enol ethers with arenediazonium salts: a new approach to the syntheses of flavonoids

被引：37

作者：

Machado, Angelo H. L. ^{[1
]}

de Sousa, Marcio A. ^{[1
]}

Patto, Daniela C. S. ^{[1
]}

Azevedo, Luis F. S. ^{[1
]}

Bombonato, Fernando I. ^{[1
]}

Correia, Carlos Roque D. ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Quim, BR-13084971 Campinas, SP, Brazil

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 11期

基金：

巴西圣保罗研究基金会;

关键词：

ELECTRON-RICH OLEFINS; PALLADIUM-CATALYZED ARYLATION; ACYL-N-VINYLAMINE; DIAZONIUM SALTS; REGIOSELECTIVE ARYLATION; ALPHA-REGIOSELECTIVITY; METHYL-ESTER; ARYL HALIDES;

D O I：

10.1016/j.tetlet.2009.01.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The scope of the Heck arylation of cyclic and acyclic enol ethers with arenediazonium salts was evaluated. Arylation of 2,3-dihydrofuran yielded 2-aryl-2,5-dihydrofurans as the major adducts (>99:1) except when using n-Bu4NHSO4 as additive or 4-NO2PhN2BF4 as arenediazonium salt. 2,3-Dihydropyran provided mixtures of the three possible isomeric Heck adducts. Arylation of n-butylvinylether with arenediazonium bearing electron-donating groups resulted in substituted acetophenones as almost exclusive products in good overall yields, Substituted 4H-chromenes provided 2-aryl-2H-chromenes in moderate yield when applying the Pd(OAc)(2)/2,6-di-t-butyl-4-methylpyridine catalytic system, which were applied in the synthesis of flavonoids. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：1222 / 1225

页数：4

共 44 条

[1] 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

[2] Dioxygen-promoted regioselective oxidative Heck arylations of electron-rich olefins with arylboronic acids [J].

Andappan, MMS ;

Nilsson, P ;

von Schenck, H ;

Larhed, M .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5212-5218

[3] Highly regioselective internal heck arylation of hydroxyalkyl vinyl ethers by aryl halides in water [J].

Arvela, Riina K. ;

Pasquini, Serena ;

Larhed, Mats .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (17) :6390-6396

[4] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[5] Heck arylation of maleic anhydrides using arenediazonium tetrafluoroborates: Synthesis of mono- and diarylated maleic anhydrides and of the marine alkaloids prepolycitrin A and polycitrin A [J].

Burtoloso, Antonio Carlos B. ;

Garcia, Ariel L. L. ;

Miranda, Karen C. ;

Correia, Carlos Roque D. .

SYNLETT, 2006, (18) :3145-3149

[6] ALPHA-REGIOSELECTIVITY IN PALLADIUM-CATALYZED ARYLATION OF ACYCLIC ENOL ETHERS [J].

CABRI, W ;

CANDIANI, I ;

BEDESCHI, A ;

PENCO, S ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1481-1486

[7] PALLADIUM-CATALYZED ARYLATION OF UNSYMMETRICAL OLEFINS - BIDENTATE PHOSPHINE LIGAND CONTROLLED REGIOSELECTIVITY [J].

CABRI, W ;

CANDIANI, I ;

BEDESCHI, A ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) :3558-3563

[8] 1,10-PHENANTHROLINE DERIVATIVES - A NEW LIGAND CLASS IN THE HECK REACTION - MECHANISTIC ASPECTS [J].

CABRI, W ;

CANDIANI, I ;

BEDESCHI, A ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7421-7426

[9] PALLADIUM-CATALYZED ALPHA-ARYLATION OF VINYL BUTYL ETHER WITH ARYL HALIDES [J].

CABRI, W ;

CANDIANI, I ;

BEDESCHI, A ;

SANTI, R .

TETRAHEDRON LETTERS, 1991, 32 (14) :1753-1756

[10] LIGAND-CONTROLLED ALPHA-REGIOSELECTIVITY IN PALLADIUM-CATALYZED ARYLATION OF BUTYL VINYL ETHER [J].

CABRI, W ;

CANDIANI, I ;

BEDESCHI, A ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3654-3655

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