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A Synthesis of Substituted ?-Allenols via Iron-Catalyzed Cross-Coupling of Propargyl Carboxylates with Grignard Reagents.

ABSTRACT: ?-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 ?-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 °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.

SUBMITTER: Kessler SN 

PROVIDER: S-EPMC5100686 | biostudies-literature | 2016 Nov

REPOSITORIES: biostudies-literature

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A Synthesis of Substituted α-Allenols via Iron-Catalyzed Cross-Coupling of Propargyl Carboxylates with Grignard Reagents.

Kessler Simon N SN   Hundemer Fabian F   Bäckvall Jan-E JE  

ACS catalysis 20160928 11

α-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 α-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 °C) and the short reaction time (15 min) allow for the presence of a variety of functional groups. Moreover, the reaction was  ...[more]

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