Synthesis of (Furyl)Methyl Disulfides via Tandem Reaction of Conjugated Ene-Yne-Ketones with Acetyl-Masked Disulfide Nucleophiles

Zhou, Xianhang; Jiang, Yuhao; Li, Jiaxin; Wang, Jinsong; Chen, Jianxin; Yu, Yue; Cao, Hua

doi:10.1021/acs.joc.3c02684

J. Org. Chem.

2024

DOI: 10.1021/acs.joc.3c02684

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Synthesis of (Furyl)Methyl Disulfides via Tandem Reaction of Conjugated Ene-Yne-Ketones with Acetyl-Masked Disulfide Nucleophiles

Xianhang Zhou,

Yuhao Jiang,

Jiaxin Li

et al.

Abstract: In this study, we outline a general method for the construction of various (furyl)methyl disulfides from acetyl-masked disulfide nucleophiles and ene-yne-ketones. This protocol is feathered by metal-free, simple experimental conditions, high efficiency, and scalable potential, which make it attractive and practical.

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Preparation of naphthalenes via Pd‐catalyzed annulation of 5‐(2‐bromophenyl)pent‐3‐en‐1‐ynes under Suzuki‐Miyaura coupling conditions

Hsu,

Liu,

Liu

2024

J Chinese Chemical Soc

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Highly substituted naphthalene derivatives were prepared via palladium‐catalyzed reaction of 5‐(2‐bromophenyl)pent‐3‐en‐1‐ynes with arylboronic acids. Typically, reaction of 3‐bromo‐4‐(3‐(4‐chlorophenyl)‐5‐phenyl‐1‐(p‐tolyl)pent‐2‐en‐4‐yn‐1‐yl)‐N‐methylaniline (1a) with PhB(OH)2 in the presence of Pd(PPh3)4 as the catalyst under basic conditions provided 8‐benzhydryl‐7‐(4‐chlorophenyl)‐N‐methyl‐5‐(p‐tolyl)naphthalen‐2‐amine (2a) quantitatively. Overall, 19 new naphthalene compounds were obtained by this methodology and their structures were characterized by spectroscopic methods. In addition, crystal structure of 2j was determined to confirm the structural details. Reaction pathway leading to the desired product is also discussed.

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Preparation of naphthalenes via Pd‐catalyzed annulation of 5‐(2‐bromophenyl)pent‐3‐en‐1‐ynes under Suzuki‐Miyaura coupling conditions

Hsu,

Liu,

Liu

2024

J Chinese Chemical Soc

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show abstract

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Synthesis of (Furyl)Methyl Disulfides via Tandem Reaction of Conjugated Ene-Yne-Ketones with Acetyl-Masked Disulfide Nucleophiles

Cited by 1 publication

References 35 publications

Preparation of naphthalenes via Pd‐catalyzed annulation of 5‐(2‐bromophenyl)pent‐3‐en‐1‐ynes under Suzuki‐Miyaura coupling conditions

Preparation of naphthalenes via Pd‐catalyzed annulation of 5‐(2‐bromophenyl)pent‐3‐en‐1‐ynes under Suzuki‐Miyaura coupling conditions

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