Palladium-catalyzed Suzuki coupling with terminal alkynes - Application to the synthesis of 2,3-disubstituted benzo[B]furans

被引：71

作者：

Colobert, F ^{[1
]}

Castanet, AS ^{[1
]}

Abillard, O ^{[1
]}

机构：

[1] Univ Strasbourg 1, ECPM, Lab Stereochim, CNRS, F-67087 Strasbourg, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 15期

关键词：

Suzuki reaction; alkynes; iodocyclisation; benzofuran; palladium;

D O I：

10.1002/ejoc.200500166

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Suzuki coupling reaction between alkynylboronic esters (generated in situ from acetylenic derivatives) and aryl bromides, pyridyl bromides or vinyl bromides is reported. 5endo-dig-iodocyclisation of o-alkynylanisoles, generated by this palladium-catalyzed Suzuki coupling reaction, was performed with N-iodosuccinimide (NIS) in the presence of BCl3. 2-Substituted 3-iodobenzo[b]furans were synthesized and transformed into 2,3-disubstituted benzo[bjfurans by Suzuki coupling reactions in high yields.((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

引用

页码：3334 / 3341

页数：8

共 37 条

[1] NEW SYNTHETIC APPLICATIONS OF WATER-SOLUBLE ACETATE PD/TPPTS CATALYST GENERATED IN-SITU - EVIDENCE FOR A TRUE PD(0) SPECIES INTERMEDIATE [J].

AMATORE, C ;

BLART, E ;

GENET, JP ;

JUTAND, A ;

LEMAIREAUDOIRE, S ;

SAVIGNAC, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6829-6839

[2] A new approach to 2,3-disubstituted benzo[b]furans from o-alkynylphenols via 5-endo-dig-iodocyclisation/palladium-catalysed reactions [J].

Arcadi, A ;

Cacchi, S ;

Fabrizi, G ;

Marinelli, F ;

Moro, L .

SYNLETT, 1999, (09) :1432-1434

[3] 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

[4] 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

[5]

ARCADI A, 1986, SYNTHESIS-STUTTGART, P749

[6] A VERSATILE 2-STAGE SYNTHESIS OF 2-SUBSTITUTED BENZO[B]FURANS FROM (2-METHOXYPHENYL)ETHYNES [J].

BUCKLE, DR ;

ROCKELL, CJM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2443-2446

[7] Heterocycles via cyclization of alkynes promoted by organopalladium complexes [J].

Cacchi, S .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :42-64

[8]

CARTER GA, 1978, ANN APPL BIOL, V88, P57, DOI 10.1111/j.1744-7348.1978.tb00679.x

[9] Suzuki-Miyaura coupling of alkynylboronic esters generated in situ from acetylenic derivatives [J].

Castanet, AS ;

Colobert, F ;

Schlama, T .

ORGANIC LETTERS, 2000, 2 (23) :3559-3561

[10] Synthesis of benzofuran derivatives on solid support via SmI2-mediated radical cyclization [J].

Du, XH ;

Armstrong, RW .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5678-5679

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