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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Rhodium-Catalyzed Formylation of Unactivated Alkyl Chlorides to Aldehydes
Peng Wang1, Yaxin Wang1, Helfried Neumann1
1Leibniz-Institut für Katalyse e. V., Albert-Einstein-Straße 29a, 18059, Rostock, Germany.
Abstract:
The first rhodium-catalyzed formylation of non-activated alkyl chlorides with syn gas (H2 /CO) allows to produce aldehydes in high yields (25 examples). A catalyst optimization study revealed Rh(acac)(CO)2 in the presence of 1,3-bisdiphenylphosphinopropane (DPPP) as the most active catalyst system for this transformation. Key for the success of the reaction is the addition of sodium iodide (NaI) to the reaction system, which leads to the formation of activated alkyl iodides as intermediates. Depending on the reaction conditions, either the linear or branched aldehydes can be preferentially obtained, which is explained by a different mechanism.
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