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Synthesis of α‐Seleno Boronates via Diboration of Carbonyl Compounds

Paul, S and Mondal, R and Geetharani, K (2023) Synthesis of α‐Seleno Boronates via Diboration of Carbonyl Compounds. In: Chemistry – An Asian Journal, 18 (22). ISSN 1861-4728

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Official URL: https://doi.org/10.1002/asia.202300761


A method has been described for accessing α-seleno alkyl boronates. The selenoboration was achieved via the diboration of carbonyl compounds to give α-oxyl boronates, which then undergo 1,2-metalate rearrangement in the presence of lithium selenolates and trifluoroacetic anhydride (TFAA). A variety of structurally diverse substrates were compatible with this protocol and efficiently provides difunctionalized products from simple starting materials. The presence of the boronic ester in the resulting organoselenium compounds serves as a versatile synthetic handle for various functionalizations. Mechanistic studies revealed that the binding of selenium nucleophile to both the boron centers in α-oxyl boronate esters. © 2023 Wiley-VCH GmbH.

Item Type: Journal Article
Publication: Chemistry – An Asian Journal
Publisher: John Wiley and Sons Ltd
Additional Information: The Copyrights for this articles belongs to the John Wiley and Sons Ltd.
Keywords: Engineering controlled terms, Esters; Selenium compounds, Engineering uncontrolled terms, 1,2-metalate rearrangement; Boronates; Boronic esters; Diboration; Diborylation; Organoselenide; Organoselenium compounds; Simple++; Trifluoroacetic anhydrides; Α-seleno boronate, Engineering main heading, Carbonyl compounds
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 13 Dec 2023 10:26
Last Modified: 13 Dec 2023 10:26
URI: https://eprints.iisc.ac.in/id/eprint/83600

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