First examples of a tosylate in the palladium-catalyzed Heck cross coupling reaction
2002; Elsevier BV; Volume: 43; Issue: 4 Linguagem: Inglês
10.1016/s0040-4039(01)02240-7
ISSN1873-3581
AutoresXiaoyong Fu, Shuyi Zhang, Jianguo Yin, Timothy L. McAllister, Sheng Jiang, Chou‐Hong Tann, T. K. Thiruvengadam, Fucheng Zhang,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoThe palladium-catalyzed cross coupling Heck reaction of tosylate (2) and methyl acrylate has been developed as an efficient method for carboncarbon bond formation. The tosylate (2) was reacted with methyl acrylate using palladium acetate as catalyst to provide 3-(3-oxo-1-cyclohexen-1-yl)-2-propenoic acid methyl ester (3) in excellent yield. The coupling reaction of tosylate (9) under the similar conditions also provided the dienoic acid methyl ester (10) in >80% overall yield. The effect of reaction parameters such as temperature and catalyst as well as the ratio of palladium acetate to triphenylphosphine on the reaction rate has been studied.
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