New, Efficient Approach for the Ligand-Free Suzuki-Miyaura Reaction of 5-Iodo-2′-deoxyuridine in Water

被引：23

作者：

Sartori, Guillaume ^{[1
]}

Herve, Gwenaelle ^{[1
]}

Enderlin, Gerald ^{[1
]}

Len, Christophe ^{[1
]}

机构：

[1] Ctr Rech Royallieu, UTC ESCOM, F-60205 Compiegne, France

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 03期

关键词：

Suzuki-Miyaura reaction; ligandless; nucleosides; green chemistry; CROSS-COUPLING REACTIONS; NUCLEOSIDE ANALOGS; ELECTRON INJECTION; PALLADIUM; DNA; FLUORESCENT; DERIVATIVES; 2'-DEOXYURIDINE; INHIBITORS; URIDINES;

D O I：

10.1055/s-0032-1317847

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 5-aryl-2'-deoxyuridines was prepared, using ligandless Suzuki-Miyaura cross-coupling reactions in neat water, starting from 5-iodo-2'-deoxyuridine as totally deprotected starting material. This ligand-free process gave good to high isolated yields within short reaction times and with low loadings of palladium.

引用

页码：330 / 333

页数：4

共 58 条

[11]

Crips G. T., 1990, TETRAHEDRON LETT, V31, P1347

[12] Suzuki cross-coupling reactions using reverse-phase glass beads in aqueous media [J].

Daku, KML ;

Newton, RF ;

Pearce, SP ;

Vile, J ;

Williams, JMJ .

TETRAHEDRON LETTERS, 2003, 44 (27) :5095-5098

[13] Suzuki-Miyaura reactions in PEG-water solutions using Pd/BaSO4 as catalytic source [J].

de Souza, Andraea Luzia F. ;

Silva, Aires da Conceicao ;

Antunes, O. A. C. .

APPLIED ORGANOMETALLIC CHEMISTRY, 2009, 23 (01) :5-8

[14]

de Vries JG, 2003, EUR J ORG CHEM, V2003, P799

[15] Very Fast Suzuki-Miyaura Reaction Catalyzed by Pd(OAc)2 under Aerobic Conditions at Room Temperature in EGME/H2O [J].

Del Zotto, Alessandro ;

Amoroso, Francesco ;

Baratta, Walter ;

Rigo, Pierluigi .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (01) :110-116

[16] 1,3-dihydrobenzolclfuran nucleoside analogues:: Additional studies of the thymine derivative [J].

Egron, D ;

Périgaud, C ;

Gosselin, G ;

Aubertin, AM ;

Faraj, A ;

Sélouane, M ;

Postel, D ;

Len, C .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (24) :4473-4475

[17] Synthesis and Spectroscopic Characterization of BODIPY-Modified Uridines as Potential Fluorescent Probes for Nucleic Acids [J].

Ehrenschwender, Thomas ;

Wagenknecht, Hans-Achim .

SYNTHESIS-STUTTGART, 2008, 22 (22) :3657-3662

[18] Supported synthesis and functionnalization of 2′-deoxyuridine by Suzuki-Miyaura cross-coupling [J].

El Kazzouli, Said ;

Berteina-Raboin, Sabine ;

Agrofoglio, Luigi A. .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2007, 26 (10-12) :1395-1398

[19] Nucleoside analogues with a novel glycone based on the benzo[c]furan core [J].

Ewing, DF ;

Fahmi, NE ;

Len, C ;

Mackenzie, G ;

Ronco, G ;

Villa, P ;

Shaw, G .

NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (11-12) :2613-2630

[20] Stereoisomeric pyrimidine nucleoside analogues based on the 1,3-dihydrobenzo[c]furan core [J].

Ewing, DF ;

Fahmi, NE ;

Len, C ;

Mackenzie, G ;

Pranzo, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (21) :3561-3565

← 1 2 3 4 5 6 →