Synthesis of new cardanol derivatives through combined iodination/palladium-catalysed cross-coupling reactions

被引：6

作者：

Arcadi, Antonio

Attanasi, Orazio. A.

Berretta, Stefano

Bianchi, Gabriele

Filippone, Paolino

机构：

[1] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67100 Laquila, Italy

[2] Univ Urbino, Ctr Studio Sostanze Organ Orgine Nat, I-61029 Urbino, Italy

来源：

SYNTHESIS-STUTTGART | 2006年 / 15期

关键词：

aromatic substitution; halogenation; palladium; Heck reaction; cross-coupling;

D O I：

10.1055/s-2006-942434

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A versatile approach to the synthesis of new cardanol derivatives through a combination of aromatic iodination of 3-n-pentadecylphenol and palladium-catalysed cross-coupling reactions has been developed. The extent of aromatic iodination is controlled by stoichiometry and affords either the mono-, di- or tri-iodo-cardanol derivatives. Suzuki, Heck and Sonogashira protocols were successfully applied for the vinylation, arylation and alkynylation of the iodo-cardanols. 2,4-Diiodo-5-n-pentadecylphenol underwent an unusual sequential regioselective dehalogenation/vinylation reaction. Sequential alkynylation/cyclisation of 2-iodo-3-n-pentadecylphenol derivatives were also investigated.

引用

收藏

页码：2523 / 2530

页数：8

相关论文

共 41 条

[1] Reductive dehalogenation of halophenols in sulfite-bisulfate medium [J].

Adimurthy, S ;

Ramachandraiah ,G .

TETRAHEDRON LETTERS, 2004, 45 (27) :5251-5252

[2] A new, environment friendly protocol for iodination of electron-rich aromatic compounds [J].

Adimurthy, S ;

Ramachandraiah, G ;

Ghosh, PK ;

Bedekar, AV .

TETRAHEDRON LETTERS, 2003, 44 (27) :5099-5101

[3]

Amorati R, 2002, SYNTHESIS-STUTTGART, P2749

[4] Absolute rate constants for the reaction of peroxyl radicals with cardanol derivatives [J].

Amorati, R ;

Pedulli, GF ;

Valgimigli, L ;

Attanasi, OA ;

Filippone, P ;

Fiorucci, C ;

Saladino, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, (11) :2142-2146

[5] A mild and versatile method for palladium-catalyzed cross-coupling of aryl halides in water and surfactants [J].

Arcadi, A ;

Cerichelli, G ;

Chiarini, M ;

Correa, M ;

Zorzan, D .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (20) :4080-4086

[6]

Arcadi A, 2002, SYNLETT, P453

[7] Electrophilic cyclization of o-acetoxy- and o-benzyloxyalkynylpyridines:: An easy entry into 2,3-disubstituted furopyridines [J].

Arcadi, A ;

Cacchi, S ;

Di Giuseppe, S ;

Fabrizi, G ;

Marinelli, F .

ORGANIC LETTERS, 2002, 4 (14) :2409-2412

[8] BETA-ARYL AND BETA-VINYL-ALPHA,BETA-DIDEHYDRO-ALPHA-AMINOACID DERIVATIVES THROUGH THE PALLADIUM-CATALYZED REACTION OF ARYL AND VINYL TRIFLATES WITH METHYL ALPHA-ACETAMIDOACRYLATE [J].

ARCADI, A ;

CACCHI, S ;

MARINELLI, F ;

MORERA, E ;

ORTAR, G .

TETRAHEDRON, 1990, 46 (20) :7151-7164

[9] Palladium-catalyzed reaction of o-ethynylphenols, o-((trimethylsilyl)ethynyl)phenyl acetates, and o-alkynylphenols with unsaturated triflates or halides: A route to 2-substituted-, 2,3-disubstituted-, and 2-substituted-3-acylbenzo[b]furans [J].

Arcadi, A ;

Cacchi, S ;

DelRosario, M ;

Fabrizi, G ;

Marinelli, F .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9280-9288

[10]

ARCADI A, 1986, SYNTHESIS-STUTTGART, P749

← 1 2 3 4 5 →