Regiodivergent C−H Annulation of Imines with Unsymmetrical Alkynes Using Transient Directing Alcohols via Rh(III) Catalysis

Liu, Bairong; Chen, Y.F.; Chen, Kairui; Liang, Qian; Liang, Yingying; Liu, Bifu; Liu, Yuan; Gao, Yang; Chen, Qian; Huo, Yanping; Li, Xianwei

doi:10.1002/adsc.202300167

Cited by 6 publications

(1 citation statement)

References 90 publications

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“…Recently, Li [40] reported a regiodivergent CÀ H annulation of imines with alkynes that features great regioselectivity, which might be attributed to the steric, electronic, and directing effect of alkynes. Notably, employing primary propargyl alcohols led to aldehyde-substituted indenones, which could be trans-formed into functionalized products.…”

Section: Metal-catalyzed Cà H Annulation With Alkynes That Contained ...mentioning

confidence: 99%

Construction of Rings via Metal‐Catalyzed C−H Annulation with Unsymmetrical Internal Alkynes: Selectivity and Applications

Zhang,

Chen,

Liu

et al. 2023

ChemCatChem

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Selective and concise construction of ring systems that are ubiquitous skeletons across chemistry, drugs, and materials is indispensable for human life. Of note, directed C‒H annulation with alkynes for the expedient delivery of ring systems holds great importance, featuring step‐ and atom‐economy, mild conditions, and broad substrate scope. However, regioselectivity issues remained when using unsymmetrical alkynes for the directed C‒H annulation. Herein, we summarized recent achievements towards solving this problem by developing catalytic systems, metal catalysts, directing groups, and alkynes with versatile and traceless functionality that ensure the overall regioselectivity, efficiency, and synthetic application. We hope this concept will promote the development of synthetic applications in the precise construction of functional molecules using C‒H annulation with unsymmetrical alkynes.

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Section: Metal-catalyzed Cà H Annulation With Alkynes That Contained ...mentioning

confidence: 99%

Construction of Rings via Metal‐Catalyzed C−H Annulation with Unsymmetrical Internal Alkynes: Selectivity and Applications

Zhang,

Chen,

Liu

et al. 2023

ChemCatChem

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Experiment and Computational Study on Pd‐Catalyzed MIA‐Directed Ortho‐C−H Alkynlation of Phenylalanine

Zhang,

Liang,

Liu

et al. 2024

Asian J Org Chem

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The direct ortho‐alkynylation of substituted phenylalanine has been successfully achieved through methoxyiminoacyl (MIA)‐mediated Pd‐catalyzed C‐H functionalization. This innovative protocol showcases the ability to apply a diverse range of phenylalanine substrates, resulting in the efficient synthesis of alkynylation benzylamine derivatives with notable effectiveness. Computational investigations further revealed that the fluoride ion enhances the electropositivity of Pd(IV) and the interaction between C1 and C2 within the transition state of the reductive elimination, which significantly expedites the reductive elimination step in the alkynylation process.

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Lewis Acid‐Catalyzed Tandem Annulation of Propargylic Alcohols with 2‐Allylphenols and Their Anti‐tumor Activities

Li,

Guo,

Liu

et al. 2024

Asian J Org Chem

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A novel bismuth(III) trifluoro‐methanesulfonate‐catalyzed and environmentally benign synthetic strategy for the construction of a wide range of structurally diverse, sophisticated [5,6,5]‐oxygen‐containing tricyclic frameworks with easy‐to handle propargylic alcohols and 2‐allylphenols as substrates in the presence of Bi(OTf)3 and AgOTf is described. This Lewis acid catalyzed [3 + 2] annulation protocol, which tolerates a great deal of functional groups, proceeds through a sequential Meyer‐Schuster rearrangement, nucleophilic substitution, 5‐exo‐trig cyclization, 5‐endo‐trig cyclization, and proton exchange sequences, affording a versatile approach for accessing oxygen‐containing tricyclic skeletons in moderate‐to‐excellent yields. In addition, most of the obtained compounds exhibited anti‐tumor activities against three types of human cancer cell lines in vitro, including Caco‐2 colon cancer cells, MCF‐7 breast cancer cells, and Hepg‐2 liver cancer cells.

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Regiodivergent C−H Annulation of Imines with Unsymmetrical Alkynes Using Transient Directing Alcohols via Rh(III) Catalysis

Cited by 6 publications

References 90 publications

Construction of Rings via Metal‐Catalyzed C−H Annulation with Unsymmetrical Internal Alkynes: Selectivity and Applications

Construction of Rings via Metal‐Catalyzed C−H Annulation with Unsymmetrical Internal Alkynes: Selectivity and Applications

Experiment and Computational Study on Pd‐Catalyzed MIA‐Directed Ortho‐C−H Alkynlation of Phenylalanine

Lewis Acid‐Catalyzed Tandem Annulation of Propargylic Alcohols with 2‐Allylphenols and Their Anti‐tumor Activities

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