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Synthesis of Benzyl-, Allyl-, and Allenyl-boronates via Copper-Catalyzed Borylation of Alcohols
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Number of Authors: 3
2017 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 19, no 5, 1204-1207 p.Article in journal (Refereed) Published
Abstract [en]

Alcohols are among the most abundant and readily available organic feedstocks in industrial processes. The direct catalytic functionalization of sp(3) C-O bonds of alcohols remains the main challenge in this field. Here, we report a copper-catalyzed synthesis of benzyl-, allyl-, and allenylboronates from benzylic, allylic, and propargylic alcohols, respectively. This protocol exhibits a broad reaction scope (40 examples) and high efficiency (up to 95% yield) under mild conditions, including for the preparation of secondary allylic boronates. Preliminarily mechanistic studies suggest that nucleophilic substitution is involved in this reaction.

Place, publisher, year, edition, pages
2017. Vol. 19, no 5, 1204-1207 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-142683DOI: 10.1021/acs.orglett.7b00256ISI: 000395726100060PubMedID: 28207271OAI: oai:DiVA.org:su-142683DiVA: diva2:1093907
Available from: 2017-05-08 Created: 2017-05-08 Last updated: 2017-05-08Bibliographically approved

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Szabó, Kálmán J.
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