Iron-Catalyzed Direct Julia-Type Olefination of Alcohols

Iron-Catalyzed Direct Julia-Type Olefination of Alcohols

Herein, we report an iron-catalyzed, convenient, and expedient strategy for the synthesis of styrene and naphthalene derivatives with the liberation of dihydrogen. The use of a catalyst derived from an earth-abundant metal provides a sustainable strategy to olefins. This method exhibits wide substra...

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Veröffentlicht in:Journal of organic chemistry 2020-08, Vol.85 (15), p.9876-9886
Hauptverfasser: Landge, Vinod G, Babu, Reshma, Yadav, Vinita, Subaramanian, Murugan, Gupta, Virendrakumar, Balaraman, Ekambaram
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container_end_page 9886
container_issue 15
container_start_page 9876
container_title Journal of organic chemistry
container_volume 85
creator Landge, Vinod G
Babu, Reshma
Yadav, Vinita
Subaramanian, Murugan
Gupta, Virendrakumar
Balaraman, Ekambaram
description Herein, we report an iron-catalyzed, convenient, and expedient strategy for the synthesis of styrene and naphthalene derivatives with the liberation of dihydrogen. The use of a catalyst derived from an earth-abundant metal provides a sustainable strategy to olefins. This method exhibits wide substrate scope (primary and secondary alcohols) functional group tolerance (amino, nitro, halo, alkoxy, thiomethoxy, and S- and N-heterocyclic compounds) that can be scaled up. The unprecedented synthesis of 1-methyl naphthalenes proceeds via tandem methenylation/double dehydrogenation. Mechanistic study shows that the cleavage of the C–H bond of alcohol is the rate-determining step.
doi_str_mv 10.1021/acs.joc.0c01173
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