Synthesis of Highly Functionalized Diaryl Ethers by Copper-Mediated O-Arylation of Phenols using Trivalent Arylbismuth Reagents

被引：33

作者：

Crifar, Cynthia ^{[1
]}

Petiot, Pauline ^{[1
]}

Ahmad, Tabinda ^{[1
]}

Gagnon, Alexandre ^{[1
]}

机构：

[1] Univ Quebec, Dept Chim, Montreal, PQ H3C 3P8, Canada

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 10期

基金：

加拿大自然科学与工程研究理事会;

关键词：

copper catalysis; functionalized diaryl ethers; O-arylation; phenols; triarylbismuthanes; PENTAVALENT ORGANOBISMUTH REAGENTS; LIGAND COUPLING REACTIONS; C-N; PHENYLATION; CHEMISTRY; ALCOHOLS; DERIVATIVES; BISMUTH(V); ENOLS; ACIDS;

D O I：

10.1002/chem.201303684

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly functionalized diaryl ethers were prepared by copper(II) acetate mediated O-arylation reaction of phenols using trivalent organobismuthanes. The reaction is performed under simple conditions and tolerates a wide diversity of functional groups on the phenol and on the organobismuth reagent. Substoichiometric amounts of catalyst can be used by performing the reaction under an oxygen atmosphere. The N-arylation of pyridones is also reported.

引用

页码：2755 / 2760

页数：6

共 59 条

[1] THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS .12. SYNTHESIS OF ISOFLAVANONES AND 3-ARYL-4-HYDROXYCOUMARINS [J].

BARTON, DHR ;

DONNELLY, DMX ;

FINET, JP ;

STENSON, PH .

TETRAHEDRON, 1988, 44 (20) :6387-6396

[2] COMPARATIVE ARYLATION REACTIONS WITH PENTAPHENYLBISMUTH AND WITH TRIPHENYLBISMUTH CARBONATE [J].

BARTON, DHR ;

BLAZEJEWSKI, JC ;

CHARPIOT, B ;

LESTER, DJ ;

MOTHERWELL, WB ;

PAPOULA, MTB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (17) :827-829

[3] TETRAPHENYLBISMUTH MONOTRIFLUOROACETATE - A NEW REAGENT FOR REGIOSELECTIVE ARYL ETHER FORMATION [J].

BARTON, DHR ;

BLAZEJEWSKI, JC ;

CHARPIOT, B ;

MOTHERWELL, WB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (10) :503-504

[4] REGIOSPECIFIC ARYLATION BY ACID-BASE CONTROLLED REACTIONS OF TETRAPHENYLBISMUTH ESTERS [J].

BARTON, DHR ;

CHARPIOT, B ;

MOTHERWELL, WB .

TETRAHEDRON LETTERS, 1982, 23 (33) :3365-3368

[5] THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS .10. STUDIES ON THE PHENYLATION AND OXIDATION OF PHENOLS [J].

BARTON, DHR ;

YADAVBHATNAGAR, N ;

FINET, JP ;

KHAMSI, J ;

MOTHERWELL, WB ;

STANFORTH, SP .

TETRAHEDRON, 1987, 43 (02) :323-332

[6] PENTAVALENT ORGANOBISMUTH REAGENTS .3. PHENYLATION OF ENOLS AND OF ENOLATE AND OTHER ANIONS [J].

BARTON, DHR ;

BLAZEJEWSKI, JC ;

CHARPIOT, B ;

FINET, JP ;

MOTHERWELL, WB ;

PAPOULA, MTB ;

STANFORTH, SP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2667-2675

[7] THE CATALYTIC EFFECT OF COPPER IONS IN THE PHENYLATION REACTION OF DAVID AND THIEFFRY [J].

BARTON, DHR ;

FINET, JP ;

PICHON, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (01) :65-66

[8] COPPER-SALTS CATALYSIS OF N-PHENYLATION OF AMINES BY TRIVALENT ORGANOBISMUTH COMPOUNDS [J].

BARTON, DHR ;

FINET, JP ;

KHAMSI, J .

TETRAHEDRON LETTERS, 1987, 28 (08) :887-890

[9] COPPER CATALYZED O-PHENYLATION OF PHENOLS AND ENOLS BY PENTAVALENT ORGANOBISMUTH COMPOUNDS [J].

BARTON, DHR ;

FINET, JP ;

KHAMSI, J ;

PICHON, C .

TETRAHEDRON LETTERS, 1986, 27 (31) :3619-3622

[10] THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS .7. THE POSSIBLE ROLE OF RADICAL MECHANISMS IN THE PHENYLATION PROCESS FOR BISMUTH(V), AND RELATED LEAD(IV), IODINE(III), AND ANTIMONY(V) REAGENTS [J].

BARTON, DHR ;

FINET, JP ;

GIANNOTTI, C ;

HALLEY, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (01) :241-249

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