Journal of Organic & Inorganic Chemistry

Stille reaction of nitro and tosyl substituted styryl bromides

6^th Edition of International Conference and Exhibition on Organic Chemistry
August 16-17, 2018 Dublin, Ireland

Antonio J Zapata V

University of Guayaquil, Ecuador

Posters & Accepted Abstracts: J Org Inorg Chem

DOI: 10.21767/2472-1123-C4-012

Abstract

The palladium-catalyzed coupling of organostannanes with organic electrophiles (Stille reaction) have become an important synthetic tool in organic chemistry. In this work, we have examined the Stille reaction of ß-nitro and ß-tosyl (ß-(p- MeC6H4SO2)) substituted styryl bromides. The ï¢ß -bromo-ßï�?­ nitrostyrenes 1 and 2 reacted with a variety of organostannanes using bis(acetonitrile)dichloropalladium(II) as catalyst and N-methylpyrrolidinone (NMP) as solvent at room temperature. Good yields of 2-nitro-1,3-dienes were obtained as a mixture of isomers. The Stille reaction of ß-bromo-ß-tosyl-styrenes 3 and 4 was also investigated. In this case, the best yields of coupling products were obtained using an excess of organotin compound (1.5 equivalents), a mixture of bis(acetonitrile)dichloropalladium(II) (5% molar) and copper iodide (10% molar) as catalysts and NMP as solvent at room temperature. Again, good yields of products, as a mixture of isomers, were obtained. The Stille reactions of ß-nitro and ß-tosyl substituted styryl bromides reported here constitute a useful synthetic tool towards the preparation of functionalized 1,3-dienes. These unsaturated molecules are among the most versatile organic compounds which participate in a wide variety of applications, including fine chemicals synthesis and polymer chemistry.

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