Gold-catalyzed cycloadditions of allenes<i>via</i>metal carbenes

Gao, Guangqin; Ma, Guang; Jiang, Xiaoyu; Liu, Qing; Fan, Cai-Ling; Lv, Dongcan; Su, Hui; Ru, Guang-Xin; Shen, Wen-Bo

doi:10.1039/d2ob00626j

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Org. Biomol. Chem.

2022

DOI: 10.1039/d2ob00626j

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Gold-catalyzed cycloadditions of allenesviametal carbenes

Guangqin Gao

Guang Ma

Xiaoyu Jiang

et al.

Abstract: This review will focus on gold-catalyzed cycloadditions of allenes as efficient methods of assembling functionalized cyclic molecules via gold carbenes.

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Cited by 9 publications

References 63 publications

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Gold(I)‐Catalyzed Cascade Cyclization of Nitrogen or Oxygen Containing Nucleophile Tethered‐Vinylidenecyclopropanes to Pyrrole, Furan, Pyrrolidine and Piperidine Skeletons

Wei

et al. 2023

Adv Synth Catal

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In this paper, we report a gold(I)catalyzed cascade cyclization of N-or O-nucleophile tethered-vinylidenecyclopropanes (VDCPs), resulting in the synthesis of pyrrole, furan, pyrrolidine, and piperidine skeletons in 30%-98% yields. Depending on the carbon chain length connecting the nucleophile and VDCPs, two reaction pathways are available, leading to different products. Both αamino VDCPs and α-hydroxyl VDCPs, where nucleophiles and VDCPs are connected by a methylene group, undergo intramolecular nucleophilic addition and aromatization, followed by ring-opening of the cyclopropane unit to produce substituted pyrroles and furans. By extending the chain length to three or four carbons, it becomes possible to form pyrrolidines and piperidines with a cyclobutene moiety via ring expansion of the cyclopropane unit, accompanied by gold carbene induced vinylogous nucleophilic addition.

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Gold(I)‐Catalyzed Cascade Cyclization of Nitrogen or Oxygen Containing Nucleophile Tethered‐Vinylidenecyclopropanes to Pyrrole, Furan, Pyrrolidine and Piperidine Skeletons

Wei

et al. 2023

Adv Synth Catal

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Regio‐ and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis

Jovanović

Tasić

et al. 2023

Adv Synth Catal

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Enallenylamides have been utilized for the synthesis of heterobicycle[4.2.0]octane derivatives via Ir/hν promoted [2+2] cycloaddition reaction. The reaction specifically targets the distal double bond of the allene moiety, and results in the exclusive formation of the trans product. The process is conducted at room temperature and under an inert atmosphere. An extensive study on the substituent propensities during the cycloaddition step revealed variable effects. Electron‐withdrawing groups conjugated with the double bond participating in the cycloaddition either hindered the process or reduced its yield. Conversely, electron‐donating substituents enhanced the efficiency, resulting in product yields ranging from 60% to 88%. Our study also demonstrated the influence of protecting groups on the reaction pathway.

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Group VIII metal difluorocarbene complexes: Synthesis and applications

Ding,

Yao,

Lin

et al. 2024

Journal of Fluorine Chemistry

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Gold-catalyzed cycloadditions of allenesviametal carbenes

Abstract: This review will focus on gold-catalyzed cycloadditions of allenes as efficient methods of assembling functionalized cyclic molecules via gold carbenes.

Cited by 9 publications

References 63 publications

Gold(I)‐Catalyzed Cascade Cyclization of Nitrogen or Oxygen Containing Nucleophile Tethered‐Vinylidenecyclopropanes to Pyrrole, Furan, Pyrrolidine and Piperidine Skeletons

Gold(I)‐Catalyzed Cascade Cyclization of Nitrogen or Oxygen Containing Nucleophile Tethered‐Vinylidenecyclopropanes to Pyrrole, Furan, Pyrrolidine and Piperidine Skeletons

Regio‐ and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis

Group VIII metal difluorocarbene complexes: Synthesis and applications

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