An efficient approach of conjugated tetraenes from butadiene and alkynesConjugated tetraenes are imp
An efficient approach of conjugated tetraenes from butadiene and alkynesConjugated tetraenes are important key substructures in electronic materials, natural products and pharmaceutical molecules. However, they are difficult to synthesize. They are conventionally prepared by repetitions of the stoichiometric reactions using phosphorus reagents and subsequent reduction and partial oxidation. For making one C=C double bond, one needs to conduct 3 step reactions by this procedure. Each process produces wastes of phosphorus oxides and metal compounds such as lithium, aluminum and manganese. Removal of organic solvents and purification processes are also required. An alternative catalytic approach is the cross-coupling reaction catalyzed by a Pd complex but this method needs to prepare an activated alkenyl or dienyl metal species in advance.TUAT researchers have achieved the new synthetic route of conjugated tetraenes from inexpensive and easily available 1,3-butadiene and substituted acetylenes by a one-pot approach under mild conditions. This is the most straightforward synthetic method ever reported. This new method has been published in the ACS journal Organometallics.“The Ru catalyst precisely distinguishes butadiene and substituted acetylene molecules and new carbon-carbon bonds are formed among a butadiene with two acetylenes just by migration of the terminal hydrogen atoms in butadiene. Interestingly, this catalysis proceeds regio- and stereoselectively and no wastes are produced from the reaction,” said Masafumi Hirano, a TUAT professor of chemistry and principal of the study.Read more. -- source link
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