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Bi-mediated allylation of aldehydes in [bmim][Br]: a mechanistic investigation.

ABSTRACT: The inexpensive room temperature ionic liquid (RTIL), [bmim][Br] has been found to be a superior medium for the Bi-mediated Barbier-type allylation of aldehydes compared to other conventional solvents. It plays the dual role of a solvent and a metal activator enabling higher yields of the products in a shorter reaction time using stoichiometric/near-stoichiometric amounts of reagents. Plausibly, [bmim][Br] activates Bi metal by a charge transfer mechanism. The ¹H VT-NMR studies suggested that both the allylating species, allylbismuth dibromide and diallylbismuth bromide, are generated in situ.

SUBMITTER: Koli M

PROVIDER: S-EPMC6122318 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Bi-mediated allylation of aldehydes in [bmim][Br]: a mechanistic investigation.

Koli Mrunesh M Chatterjee Sucheta S Chattopadhyay Subrata S Goswami Dibakar D

Beilstein journal of organic chemistry 20180822

The inexpensive room temperature ionic liquid (RTIL), [bmim][Br] has been found to be a superior medium for the Bi-mediated Barbier-type allylation of aldehydes compared to other conventional solvents. It plays the dual role of a solvent and a metal activator enabling higher yields of the products in a shorter reaction time using stoichiometric/near-stoichiometric amounts of reagents. Plausibly, [bmim][Br] activates Bi metal by a charge transfer mechanism. The <sup>1</sup>H VT-NMR studies sugges ...[more]

PMID: 30202472

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