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Iridium-Catalyzed Alkene-Selective Transfer Hydrogenation with 1,4-Dioxane as Hydrogen Donor

Deliang Zhang, Tomohiro Iwai*, Masaya Sawamura*

*Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan, Email: iwai-tsci.hokudai.ac.jp, sawamurasci.hokudai.ac.jp

D. Zhang, T. Iwai, M. Sawamura, Org. Lett., 2019, 21, 5867-5872.

DOI: 10.1021/acs.orglett.9b01989 (free Supporting Information)


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Abstract

The use of 1,2-bis(dicyclohexylphosphino)ethane (DCyPE) as ligand enabled an iridium-catalyzed transfer hydrogenation of alkenes using 1,4-dioxane as a hydrogen donor. A polystyrene-cross-linking bisphosphine PS-DPPBz produced a reusable heterogeneous catalyst. The reaction tolerates other potentially reducible functional groups such as carbonyl, nitro, cyano, and imino groups.


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Key Words

reduction of alkenes, 1,4-reduction of α,β-unsaturated compounds, 1,4-dioxane


ID: J54-Y2019