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Iron-Catalyzed Cross-Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols.

ABSTRACT: Herein we disclose an iron-catalyzed cross-coupling reaction of propargyl ethers with Grignard reagents. The reaction was demonstrated to be stereospecific and allows for a facile preparation of optically active allenes via efficient chirality transfer. Various tri- and tetrasubstituted fluoroalkyl allenes can be obtained in good to excellent yields. In addition, an iron-catalyzed cross-coupling of Grignard reagents with α-alkynyl oxetanes and tetrahydrofurans is disclosed herein, which constitutes a straightforward approach towards fully substituted β- or γ-allenols, respectively.

SUBMITTER: Posevins D

PROVIDER: S-EPMC8518087 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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Iron-Catalyzed Cross-Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols.

Posevins Daniels D Bermejo-López Aitor A Bäckvall Jan-E JE

Angewandte Chemie (International ed. in English) 20210902 41

Herein we disclose an iron-catalyzed cross-coupling reaction of propargyl ethers with Grignard reagents. The reaction was demonstrated to be stereospecific and allows for a facile preparation of optically active allenes via efficient chirality transfer. Various tri- and tetrasubstituted fluoroalkyl allenes can be obtained in good to excellent yields. In addition, an iron-catalyzed cross-coupling of Grignard reagents with α-alkynyl oxetanes and tetrahydrofurans is disclosed herein, which constitu ...[more]

PMID: 34318557

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