Preparation of Arylphosphonates by Palladium(0)-Catalyzed Cross-Coupling in the Presence of Acetate Additives: Synthetic and Mechanistic Studies

被引：142

作者：

Kalek, Marcin ^{[1
]}

Jezowska, Martina ^{[1
]}

Stawinski, Jacek ^{[1
,2
]}

机构：

[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden

[2] Polish Acad Sci, Inst Bioorgan Chem, PL-61704 Poznan, Poland

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 18期

基金：

瑞典研究理事会;

关键词：

acetate additives; arylphosphonates; H-phosphonate diesters; nucleotide analogues; palladium-catalyzed cross-coupling; PALLADIUM-CATALYZED SYNTHESIS; CARBON BOND FORMATION; ENANTIOSELECTIVE SYNTHESIS; ZEROVALENT PALLADIUM; OXIDATIVE ADDITION; STEREOSELECTIVE-SYNTHESIS; PHOSPHONATE COMPLEXES; PEPTIDE-SYNTHESIS; PHOSPHINE LIGAND; NUCLEIC-ACIDS;

D O I：

10.1002/adsc.200900590

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient protocol for the synthesis of arylphosphonate diesters via a palladium-catalyzed cross-coupling of H-phosphonate diesters with aryl electrophiles, promoted by acetate ions, was developed. A significant shortening of the cross-coupling time in the presence of the added acetate ions was achieved for bidentate and monodentate supporting ligands, and for different aryl electrophiles (iodo, bromo and triflate derivatives). The reaction conditions were optimized in terms of amount of the catalyst, supporting ligands, and source of the acetate ion used. Various arylphosphonates, including those of potential biological significance, were synthesized using this newly developed protocol. Some mechanistic aspects of the investigated reactions are also discussed.

引用

页码：3207 / 3216

页数：10

共 69 条

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