Magnesium-mediated hydroboration under ambient condition: A reduction of esters, aldehydes, and ketones

Alkoxymagnesium halide is demonstrated as an effective catalyst for the carbonyl hydroboration of esters, aldehydes, and ketones. This study reports the smooth hydroboration of a variety of esters, aldehydes, and ketones with ethoxymagnesium chloride (EtOMgCl) and pinacolborane under mild reaction c...

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Bibliographic Details
Published in:Tetrahedron 2023-08, Vol.142, p.133500, Article 133500
Main Authors: Han, Hyun Ji, Kim, Hyun Tae, Kim, Jaeho, Jaladi, Ashok Kumar, An, Duk Keun
Format: Article
Language:English
Subjects:
Aldehydes and ketones
Catalytic hydroboration
Esters
Ethoxymagnesium chloride (EtOMgCl)
Pinacolborane (HBpin)
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Summary:Alkoxymagnesium halide is demonstrated as an effective catalyst for the carbonyl hydroboration of esters, aldehydes, and ketones. This study reports the smooth hydroboration of a variety of esters, aldehydes, and ketones with ethoxymagnesium chloride (EtOMgCl) and pinacolborane under mild reaction conditions (low catalyst loading 0.3 mol% for aldehydes and ketones, 5 mol% for esters, room temperature). Among the tested alkoxymagnesium chlorides, EtOMgCl was the optimum catalyst in terms of yield and selectivity for esters. Moreover, the designed protocol afforded the chemoselective hydroboration of esters in good yields with high selectivity. To create your abstract, type over the instructions in the template box below. Fonts or abstract dimensions sh ould not be changed or altered. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2023.133500