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Organic Chemistry 2018 Journal of Organic & Inorganic Chemistry
ISSN: 2472-1123 Page 42
August 16-17, 2018
Dublin, Ireland
6th Edition of International
Conference and Exhibition on
Organic Chemistry
T he 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 ß -bromo-ßnitro-
styrenes 1 and 2 reacted with a variety of organostannanes using
bis(acetonitrile)dichloropalladium(II) as catalyst and N-methyl-
pyrrolidinone (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
amixture 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.
Stille reaction of β-nitro and β-tosyl substituted styryl
bromides
Antonio J Zapata V
University of Guayaquil, Ecuador
J Org Inorg Chem 2018, Volume 4
DOI: 10.21767/2472-1123-C4-012