Protocol for the synthesis of homoallenic alcohols via allenyl radical-mediated allenylation of alkenes

Review Chemistry, Multidisciplinary

Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

Jose M. Alonso et al.

Summary: The allene functionality, specifically the allenol, has evolved from a chemical curiosity to a common building block in modern organic chemistry, with unique reactivity and frequent occurrence in naturally systems. This Review highlights the significant contributions to the chemistry of allenols in the past decade, focusing on their synthesis, reactivity, and presence in natural products.

CHEMICAL REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Alkene Difunctionalization Triggered by a Stabilized Allenyl Radical: Concomitant Installation of Two Unsaturated C-C Bonds

Yunlong Wei et al.

Summary: The radical-mediated difunctionalization of alkenes introduces one alkenyl or alkynyl group to target compounds, but simultaneous installation of two unsaturated C-C bonds via alkene difunctionalization remains challenging due to the high instability of alkenyl and alkynyl radicals. This study reports the successful photocatalytic 1,2-alkynylalkenylation and 1,2-enynylalkenylation of alkenes, utilizing stabilized allenyl radicals for intermolecular addition, with a broad substrate scope and increased degree of unsaturation.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

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

Daniels Posevins et al.

Summary: An iron-catalyzed cross-coupling reaction of propargyl ethers with Grignard reagents was disclosed, allowing for efficient chirality transfer and preparation of various fluoroalkyl allenes. Additionally, an iron-catalyzed cross-coupling of Grignard reagents with alpha-alkynyl oxetanes and tetrahydrofurans was demonstrated as a straightforward approach towards fully substituted beta- or gamma-allenols.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Review Chemistry, Multidisciplinary