Preparation of Arylphosphonates by Palladium(0)-Catalyzed Cross-Coupling in the Presence of Acetate Additives: Synthetic and Mechanistic Studies
Preparation of Arylphosphonates by Palladium(0)-Catalyzed Cross-Coupling in the Presence of Acetate Additives: Synthetic and Mechanistic Studies
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DOI：
10.1002/adsc.200900590
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发表时间：
2009-12-01
影响因子：
5.4
通讯作者：
Stawinski, Jacek
中科院分区：
文献类型：
--
作者：
Kalek, Marcin;Jezowska, Martina;Stawinski, Jacek
研究了钯催化h -膦酸二酯与芳基亲电试剂在醋酸离子催化下的交叉偶联反应合成芳基膦酸二酯的方法。对于双齿和单齿支撑配体，以及不同的芳基亲电试剂（碘、溴和三氟酸衍生物），在醋酸离子的存在下，交叉偶联时间显著缩短。从催化剂用量、配体用量、醋酸离子来源等方面对反应条件进行了优化。各种芳基膦酸盐，包括那些潜在的生物学意义，合成使用这个新开发的方案。还讨论了所研究反应的一些机理方面。
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.