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Mass Efficiency of Alkene Syntheses with Tri- and Tetrasubstituted Double Bonds

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journal contribution
posted on 22.10.2017, 00:00 by Marco Eissen, Dieter Lenoir
Environmental factors and process mass intensity were determined and evaluated for more than 30 standard procedures for the synthesis of alkenes with tri- and tetrasubstituted double bonds. They contain some of the most commonly used reaction types for the synthesis of alkenes, e.g., Peterson, Shapiro, Heck, Suzuki, and Negishi. Four kinds of syntheses of geminal dihalides were also considered. The highest efficiency is found when employing the olefin metathesis reaction followed by other modern catalytic processes, and the lowest efficiency is found with the Julia–Lythgoe process. Several types of McMurry coupling reactions show that the efficiency is dependent on the variant of this type of reaction. These metrics point out weaknesses as well as optimization potentials and show which performances can be expected. This could provide an orientation when mass efficiency aspects are relevant during the synthesis planning of alkenes with tri- and tetrasubstituted double bonds.