Revisiting the Hirao cross-coupling: improved synthesis of aryl and heteroaryl phosphonates

被引:126
作者
Belabassi, Yamina [1 ]
Alzghari, Saeed [1 ]
Montchamp, Jean-Luc [1 ]
机构
[1] Texas Christian Univ, Dept Chem, Ft Worth, TX 76129 USA
关键词
cross-coupling; phosphorus; palladium; heterocycles; aryl halides;
D O I
10.1016/j.jorganchem.2008.07.020
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The palladium-catalyzed cross-coupling of dialkylphosphite with aromatic electrophiles (Hirao coupling) was re-investigated. Some limitations in terms of palladium loadings and substrate reactivity are alleviated with the use of Pd(OAc)(2) complexed to 1,1'-bis(diphenylphosphino) ferrocene (dppf) as a ligand. Various aryl and heteroaryl halides are employed to deliver both known and novel substituted phosphonates. The first examples of aryl chloride couplings are also reported. (C) 2008 Elsevier B.V. All rights reserved.
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页码:3171 / 3178
页数:8
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