Gadge Sandip T, Bhanage Bhalchandra M
Department of Chemistry, Institute of Chemical Technology, N. Parekh Marg, Matunga, Mumbai-400019, India.
Org Biomol Chem. 2014 Aug 14;12(30):5727-32. doi: 10.1039/c4ob00729h. Epub 2014 Jun 26.
This work reports a mild, stable and efficient Pd(OAc)2/DABCO catalysed protocol for the synthesis of single and double Weinreb amides. Double Weinreb amides, having 1,4-phenylene- and biphenylene-linkers - important backbones for the synthesis of biologically active symmetrical resorcylate oligomer units - were synthesized by the double carbonylation of aryl diiodides. Notably, the reaction does not require any expensive or air/moisture sensitive phosphine ligands. DABCO was found to be an inexpensive and stable ligand for the Pd(OAc)2 catalysed carbonylation of aryl iodides under an atmospheric pressure of carbon monoxide, and offered excellent yields of the single and double Weinreb amides.
本研究报道了一种温和、稳定且高效的由醋酸钯/1,4-二氮杂双环[2.2.2]辛烷（DABCO）催化合成单、双Weinreb酰胺的方法。具有1,4-亚苯基和联亚苯基连接基的双Weinreb酰胺是合成生物活性对称间苯二甲酸酯低聚物单元的重要骨架，通过芳基二碘化物的双羰基化反应合成。值得注意的是，该反应不需要任何昂贵或对空气/湿气敏感的膦配体。研究发现，在一氧化碳常压下，1,4-二氮杂双环[2.2.2]辛烷是醋酸钯催化芳基碘化物羰基化反应的一种廉价且稳定的配体，能以优异的产率得到单、双Weinreb酰胺。
