The Halogen–Samarium Exchange Reaction: Synthetic Applications and Kinetics

Lucile Anthore-Dalion, Andreas D. Benischke, Baosheng Wei, Guillaume Berionni, Paul Knochel

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Résumé

Fast I/Sm and Br/Sm exchanges take place when
various aromatic or heterocyclic iodides and bromides are
treated with nBu2SmCl·4LiCl and nBu3Sm·5LiCl, respectively.
The resulting organosamarium reagents were efficiently
quenched with aldehydes, ketones, and imines. Also, they
undergo acylations when treated with N,N-dimethylamides
leading to ketones. The rate of the Br/Sm exchange for a typical
aryl bromide was determined and found to be 8.5 x 105 faster
than the Br/Mg exchange, indicating that the rate of a metalexchange
is related to the ionic character of the carbon–metal
bond and to the metal electronegativity.
langue originaleAnglais
Pages (de - à)4046-4050
Nombre de pages5
journalAngewandte Chemie International Edition
Volume58
Numéro de publication12
Date de mise en ligne précoce2019
Les DOIs
Etat de la publicationPublié - 18 mars 2019

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