Preparation of 3-O-aryl chloramphenicol derivatives via chemoselective copper-catalyzed O-arylation of (1R,2R)-(-)-N-BOC2-amino-1-(4-nitropheny1)-1,3-propanediol using triarylbismuthines

被引：13

作者：

Ahmad, Tabinda ^{[1
]}

Dansereau, Julien ^{[1
]}

Hebert, Martin ^{[1
]}

Grand-Maitre, Chantal ^{[2
]}

Larivee, Alexandre ^{[2
]}

Siddiqui, Arshad ^{[2
]}

Gagnon, Alexandre ^{[1
]}

机构：

[1] Univ Quebec, Dept Chim, CP 8888,Succursale Ctr Ville, Montreal, PQ H3C 3P8, Canada

[2] Paraza Pharma Inc, 7171 Rue Frederick Banting, Montreal, PQ H4S 1Z9, Canada

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 38期

基金：

加拿大自然科学与工程研究理事会;

关键词：

Organobismuthines; Chemoselective O-arylation; Copper catalysis; Chloramphenicol; C-O bond formation; TRIVALENT ORGANOBISMUTH REAGENTS; CROSS-COUPLING REACTION; N-ARYLATION; CARBONYL-COMPOUNDS; DOMINO SYNTHESIS; ALPHA-ARYLATION; BOND FORMATION; BISMUTH BOND; PHENYLATION; PALLADIUM;

D O I：

10.1016/j.tetlet.2016.08.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed protocol for the chemoselective arylation of (1R,2R)-(-)-N-B0C-2-amino-1-(4-nitrophenyl)-1,3-propanediol using triarylbismuth reagents is reported. The reaction operates under simple and mild conditions, shows good functional group tolerance and allows the installation of ortho-, meta-, and para-substituted aryl groups in moderate to good yields. These arylated products are then transformed in two steps into their corresponding N-dichloroacetamide derivatives. This sequence provides an expedient access to 3-O-aryl chloramphenicol derivatives. (C)2016 Elsevier Ltd. All rights reserved.

引用

页码：4284 / 4287

页数：4

共 74 条

[1] TETRAHEDRON REPORT .235. NEWER METHODS OF ARYLATION [J].

ABRAMOVITCH, RA ;

BARTON, DHR ;

FINET, JP .

TETRAHEDRON, 1988, 44 (11) :3039-3071

[2] MONOESTERS OF CHLORAMPHENICOL, ESTERIFIED ON SECONDARY HYDROXYL GROUP IN PRESENCE OF TRIFLUOROACETIC ANHYDRIDE AND METHANESULFONIC ANHYDRIDE [J].

ALMIRANTE, L ;

TOSOLINI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (01) :177-&

[3] The chemistry of pentavalent organobismuth reagents .14. Recent advances in the copper-catalyzed phenylation of amines. [J].

Arnauld, T ;

Barton, DHR ;

Doris, E .

TETRAHEDRON, 1997, 53 (12) :4137-4144

[4] 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

[5] COPPER CATALYZED PHENYLATION OF INDOLES BY TRIPHENYLBISMUTH BIS-TRIFLUOROACETATE [J].

BARTON, DHR ;

FINET, JP ;

KHAMSI, J .

TETRAHEDRON LETTERS, 1988, 29 (10) :1115-1118

[6] METALLIC COPPER CATALYSIS OF N-ARYLATION OF AMINES BY TRIARYLBISMUTH DIACYLATES [J].

BARTON, DHR ;

FINET, JP ;

KHAMSI, J .

TETRAHEDRON LETTERS, 1986, 27 (31) :3615-3618

[7] 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

[8] BISMUTH(V) REAGENTS IN ORGANIC-SYNTHESIS [J].

BARTON, DHR ;

FINET, JP .

PURE AND APPLIED CHEMISTRY, 1987, 59 (08) :937-946

[9] Neutral organoantimony(III) and organobismuth(III) ligands as acceptors in transition metal complexes - Role of substituents and co-ligands [J].

Benjamin, Sophie L. ;

Reid, Gillian .

COORDINATION CHEMISTRY REVIEWS, 2015, 297 :168-180

[10] ANALOGS OF CHLORAMPHENICOL - CIRCULAR-DICHROISM SPECTRA, INHIBITION OF RIBOSOMAL PEPTIDYLTRANSFERASE, AND POSSIBLE MECHANISM OF ACTION [J].

BHUTA, P ;

CHUNG, HL ;

HWANG, JS ;

ZEMLICKA, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (12) :1299-1305

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