Alkenes function as versatile synthetic springboards due to a wide variety of functional motifs available through different addition reactions. Therefore, access to alkenes of a specific stereoisomer at a designated position in a molecule can unlock more facile pathways for the production of compounds with desired physical and chemical properties. The catalyst cis-Mo(CO)4(PCy3)2 was designed to selectively isomerize terminal alkenes to (Z)-2-alkenes. Reaction conditions were optimized to maximize selectivity towards the thermodynamically unfavorable Z-isomer and conversion to the 2-alkene for a diverse substrate scope. Selectivity ratios as high as 20:1 Z:E and near quantitative conversion were observed with low catalyst loadings and a single acid additive under mild conditions. A mechanistic study was undertaken to gain an insight into the active species involved in the migration and isomerization process.

Regiospecific and stereoselective transformation of terminal alkenes to (Z)-2-alkenes with a molybdenum(0) complex

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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