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Synthesis of Vinyl-, Allyl-, and 2-Boryl Allylboronates via a Highly Selective Copper-Catalyzed Borylation of Propargylic Alcohols
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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Number of Authors: 5
2017 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 19, no 24, 6586-6589 p.Article in journal (Refereed) Published
Abstract [en]

An efficient methodology for the synthesis of vinyl-, allyl-, and (E)-2-boryl allylboronates from propargylic alcohols via Cu-catalyzed borylation under mild conditions is reported. In the presence of commercially available Cu(OAc)(2) or Cu(acac)(2) and Xantphos, the reaction affords the desired products in up to 92% yield with a broad substrate scope (43 examples). Isolation of an allenyl boronate as the reaction intermediate suggests that an insertion elimination-type reaction, followed by borylcupration, is involved in the borylation of propargylic alcohols.

Place, publisher, year, edition, pages
2017. Vol. 19, no 24, 6586-6589 p.
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Organic Chemistry
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URN: urn:nbn:se:su:diva-150921DOI: 10.1021/acs.orglett.7b03294ISI: 000418392400032PubMedID: 29181971OAI: oai:DiVA.org:su-150921DiVA: diva2:1172174
Available from: 2018-01-09 Created: 2018-01-09 Last updated: 2018-01-09Bibliographically approved

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