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Iron-Catalyzed Borylation of Propargylic Acetates for the Synthesis of Multisubstituted Allenylboronates
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-8257-8708
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-5212-8255
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-7826-6445
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Number of Authors: 62023 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 29, no 3, article id e202203130Article in journal (Refereed) Published
Abstract [en]

A novel iron-catalyzed borylation of propargylic acetates leading to allenylboronates has been developed. The method allows the preparation of a variety of di-, tri- and tetrasubstituted allenylboronates at room temperature with good functional group compatibility. Stereochemical studies show that an anti-SN2’ displacement of acetate by boron occurs; this also allows transfer of chirality to yield enantiomerically enriched allenylboronates. The synthetic utility of this protocol was further substantiated by transformations of the obtained allenylboronates including oxidation and propargylation. 

Place, publisher, year, edition, pages
2023. Vol. 29, no 3, article id e202203130
Keywords [en]
Allenes, allenylboronates, borylation, iron, propargyl esters
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-213118DOI: 10.1002/chem.202203130ISI: 000888153700001PubMedID: 36250587Scopus ID: 2-s2.0-85143203381OAI: oai:DiVA.org:su-213118DiVA, id: diva2:1721016
Available from: 2022-12-20 Created: 2022-12-20 Last updated: 2023-02-23Bibliographically approved

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Bermejo-López, AitorKong, Wei-JunTortajada, Pedro JesusPosevins, DanielsMartín‐Matute, BelénBäckvall, Jan-E.

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