Recent advances in free radical cyclizations of 2-alkenyl benzaldehydes to synthesize benzocycloketones

Chen, Pu; Ji, Xiaochen; Tang, Shi; Deng, Guo‐Jun; Huang, Huawen

doi:10.1039/d2nj04021b

New J. Chem.

2022

DOI: 10.1039/d2nj04021b

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Recent advances in free radical cyclizations of 2-alkenyl benzaldehydes to synthesize benzocycloketones

Pu Chen

Xiaochen Ji

Shi Tang

et al.

Abstract: The radical cyclization of 2-alkenyl benzaldehyde derivatives has received great attention over the past few decades and it provides a new route for the synthesis of a large number of...

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2024

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Cited by 4 publications

References 108 publications

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Photochemical Radical Cascade 6‐endo Cyclization of Dienes with α‐Carbonyl Bromides for the Synthesis of Six‐Membered Benzo‐Fused Lactams

Sui,

Guo,

Xiong

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryA novel visible‐light‐induced radical cascade 6‐endo cyclization of dienes (N‐(2‐vinylphenyl)acryl amides) is developed utilizing α‐carbonyl bromides as alkyl reagents. This approach affords an efficient way for synthesizing six‐membered benzo‐fused lactam derivatives with chemo‐ and regio‐selectivity and good functional group tolerance. Primary, secondary, and tertiary bromides are well‐compatible with this cascade cyclization reaction.

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Photochemical Radical Cascade 6‐endo Cyclization of Dienes with α‐Carbonyl Bromides for the Synthesis of Six‐Membered Benzo‐Fused Lactams

Sui,

Guo,

Xiong

et al. 2024

Chin. J. Chem.

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Photocatalytic Synthesis of Indanone, Pyrone, and Pyridinone Derivatives with Diazo Compounds as Radical Precursors

Xie,

Bao,

Zhuo

et al. 2024

Org. Lett.

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We disclose herein a photocatalytic radical cascade cyclization of diazoalkanes for the divergent synthesis of important carbocycles and heterocycles. Under the optimal reaction conditions, various indanone, pyrone, and pyridinone derivatives can be obtained in moderate to good yields. Mechanistic experiments support the formation of carbon-centered radicals from diazoalkanes through the proton-coupled electron transfer process. Scale-up reaction using continuous flow technology and useful downstream application of the formed heterocycles further render the strategy attractive and valuable.

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Copper-Catalyzed 1,2-Sulfonyletherification of 1,3-Dienes

Chen,

Tian,

et al. 2024

Org. Lett.

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A selective three-component 1,2-sulfonyl etherification of aryl 1,3-dienes enabled by copper catalysis to afford biologically interesting alkenyl 1,2-sulfone ether derivatives through C−S and C−O bond formation is described. The protocol proceeds with the sulfonyl chloride and alcohols under simple, mild, and base-free conditions, providing a straightforward route to sulfonylated allyl ether compounds with broad functional group tolerance and excellent chemo-and regioselectivity. Mechanistic studies indicate that the selective alkene difunctionalization includes a key copper-mediated single-electron transfer process.

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Recent advances in free radical cyclizations of 2-alkenyl benzaldehydes to synthesize benzocycloketones

Abstract: The radical cyclization of 2-alkenyl benzaldehyde derivatives has received great attention over the past few decades and it provides a new route for the synthesis of a large number of...

Cited by 4 publications

References 108 publications

Photochemical Radical Cascade 6‐endo Cyclization of Dienes with α‐Carbonyl Bromides for the Synthesis of Six‐Membered Benzo‐Fused Lactams

Photochemical Radical Cascade 6‐endo Cyclization of Dienes with α‐Carbonyl Bromides for the Synthesis of Six‐Membered Benzo‐Fused Lactams

Photocatalytic Synthesis of Indanone, Pyrone, and Pyridinone Derivatives with Diazo Compounds as Radical Precursors

Copper-Catalyzed 1,2-Sulfonyletherification of 1,3-Dienes

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