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A Synthesis of Substituted alpha-Allenols via Iron-Catalyzed Cross-Coupling of Propargyl Carboxylates with Grignard Reagents
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry. Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Number of Authors: 3
2016 (English)In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 6, no 11, 7448-7451 p.Article in journal (Refereed) Published
Abstract [en]

alpha-Allenols are attractive and versatile compounds whose preparation can be a nontrivial task. In this Letter, we provide a method for the prompt synthesis of substituted alpha-allenols via a catalytic cross-coupling reaction which makes use of a nontoxic and cost-effective iron catalyst. The catalyst loading is typically as low as 1-5 mol %. The mild reaction conditions (-20 degrees C) and the short reaction time (15 min) allow for the presence of a variety of functional groups. Moreover, the reaction was shown to be scalable up to gram scale and the propargyl substrates are readily accessible by a one-pot synthesis.

Place, publisher, year, edition, pages
2016. Vol. 6, no 11, 7448-7451 p.
Keyword [en]
iron catalysis, cross coupling, allenol, allenyl acetate, Grignard reagents
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-136751DOI: 10.1021/acscatal.6b02114ISI: 000387306100021PubMedID: 27840771OAI: oai:DiVA.org:su-136751DiVA: diva2:1056458
Available from: 2016-12-14 Created: 2016-12-14 Last updated: 2016-12-14Bibliographically approved

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Hundemer, FabianBäckvall, Jan-E.
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