Recent Advances in Palladium‐Catalyzed Asymmetric Heck/Tsuji–Trost Reactions of 1,n‐Dienes

Zhao, Guofeng; Li, Wenbo; Zhang, Junliang

doi:10.1002/chem.202400076

Cited by 5 publications

References 124 publications

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Asymmetric Alkylative Difunctionalization of Carbon–Carbon Double Bonds by Aliphatic C─H Bond Activation

Yan,

Wang,

Mao

et al. 2024

ChemCatChem

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This Concept highlights the latest advancements in asymmetric alkylative difunctionalization of carbon‐carbon double bonds by utilizing aliphatic C–H substrates as alkyl radical precursors. By integrating different hydrogen atom transfer (HAT) process with various transition metal catalytic systems, various alkane substrates can be efficiently converted into corresponding alkyl radicals, which then participate in radical additions to carbon‐carbon double bonds followed by stereoselective functionalizations with a 3rd‐component. These strategies leverage inexpensive, abundant, and readily available alkane feedstocks to rapidly construct complex chiral molecules, demonstrating high step‐ and atom‐economy. This Concept focuses on recent progress and applications of this area, provides a comprehensive perspective on current developments and suggests future directions in alkane‐involved asymmetric transformations.

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Asymmetric Alkylative Difunctionalization of Carbon–Carbon Double Bonds by Aliphatic C─H Bond Activation

Yan,

Wang,

Mao

et al. 2024

ChemCatChem

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Regio‐, Site‐ and Stereo‐Selective Aziridination of Conjugated Dienes Enabled by Palladium/Copper/Iodide/Oxygen Cooperation

Meng,

Wang,

Zhang

et al. 2024

Chemistry A European J

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Vinylaziridines are important building blocks in organic chemistry, especially in the synthesis of nitrogen‐containing heterocycles. The direct and efficient transfer of an appropriate nitrogen source to readily accessible conjugated dienes is a notable methodology. The Pd‐catalyzed oxidative 1,2‐difunctionalization of conjugated dienes through a π‐allyl‐palladium species should be an ideal method for the selective synthesis of vinylaziridines. However, this method faces the challenge of regioselectivity, often resulting in 1,4‐difunctionalization instead. In this study, we developed a Pd‐catalyzed aerobic 1,2‐difunctionalization of conjugated dienes via a π‐allyl‐palladium species to achieve regio‐, site‐ and stereo‐selective aziridination under the synergistic effects of Pd(II), Cu(I), I‐, and O2. The π‐allyl palladium species formed in the system undergoes an unusual iodination process, leading to the formation of an allyl iodide intermediate. Subsequently, the vinylaziridine is obtained through intramolecular SN2' substitution of the allyl iodide.

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Enantioselective synthesis of α-chiral sulfonates through palladium-catalyzed Tsuji–Trost sulfonylation with sulfur dioxide

He,

Zhou,

Wang

et al. 2025

Org. Chem. Front.

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Recent Advances in Palladium‐Catalyzed Asymmetric Heck/Tsuji–Trost Reactions of 1,n‐Dienes

Cited by 5 publications

References 124 publications

Asymmetric Alkylative Difunctionalization of Carbon–Carbon Double Bonds by Aliphatic C─H Bond Activation

Asymmetric Alkylative Difunctionalization of Carbon–Carbon Double Bonds by Aliphatic C─H Bond Activation

Regio‐, Site‐ and Stereo‐Selective Aziridination of Conjugated Dienes Enabled by Palladium/Copper/Iodide/Oxygen Cooperation

Enantioselective synthesis of α-chiral sulfonates through palladium-catalyzed Tsuji–Trost sulfonylation with sulfur dioxide

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