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‘One-pot’ synthesis of conjugated polyenes

By Tetsuo Satoh |

The research group of professor Masafumi Hirando at Tokyo University of Agriculture and Technology (TUAT; Koganei City, Japan; www.tuat.ac.jp) has performed the world’s first one-pot synthesis of conjugated polyenes, which normally require at least seven steps by conventional methods. This shortens the synthesis time from around a week to as little as 30 minutes. Waste generation is virtually eliminated due to the hydrogen transfer reaction, which enables regio- and stereo-selective reactions for making precursors for electronics chemicals, vitamins and pharmaceuticals. At room temperature, the new synthesis approach directly produces conjugated tetraenes with 85% yield by reacting 1,3-butadiene over a Ru(0) catalyst containing two internal alkyne ligands. The stoichiometric reaction of [Ru(η4-cisoid-1,3-butadiene)(η4-1,5-COD)(NCMe)] with two equivalents of 3-hexyne produces a tetraene complex of Ru(0), [Ru{3–6-η4-(3E,5E,7E,9E)-4,9-diethyldodeca-3,5,7,9-tetraene}(η4-1,5-COD)(NCMe)], in 98% yield. When exposed to 1,3-butadiene, the conjugated tetraene ligand is released with 92% yield. The study is described in a recent issue of Organometallics.
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