Controllable cyclization of alkynyl thioethers<i>via</i>Brønsted acid-catalyzed dearomatization

Fan, Xin-Yang; Liu, Xin; Zhu, Bo‐Han; Lin, Jianguo; Qian, Peng‐Cheng; Zhou, Bo; Ye, Long‐Wu

doi:10.1039/d3qo00489a

Org. Chem. Front.

2023

DOI: 10.1039/d3qo00489a

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Controllable cyclization of alkynyl thioethersviaBrønsted acid-catalyzed dearomatization

Xin-Yang Fan

Xin Liu

Bo‐Han Zhu

et al.

Abstract: An efficient Brønsted acid-catalyzed formal alkyne hydroarylation of phenol-alkynyl thioethers via dearomatization and rearrangement is described. This protocol enables the practical and atom-economic synthesis of valuable phenanthrols in generally excellent...

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Cited by 5 publications

References 71 publications

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Copper‐Catalyzed Dearomative Cyclization of Indolyl Ynamides for Synthesis of Pentacyclic Spiroindolines

Xu,

Jiang,

Dong

et al. 2024

Adv Synth Catal

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The dearomatization of indoles with ynamides is a convenient access towards polycyclic spiroindolines, which can be initiated by α‐ and β‐additions of ynamides. Currently, the related β‐addition initiated dearomative cyclization requires noble‐metal catalyst or stoichiometric oxidant. Herein, we report a copper‐catalyzed dearomative cyclization of aryl‐substituted indolyl ynamides through regioselective β‐addition onto ynamides, providing pentacyclic spiroindolines in 81–97% yields with >25:1 diastereoselectivities. Moreover, preliminary success has been obtained for the catalytic enantioselective dearomative cyclization.

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Copper‐Catalyzed Dearomative Cyclization of Indolyl Ynamides for Synthesis of Pentacyclic Spiroindolines

Xu,

Jiang,

Dong

et al. 2024

Adv Synth Catal

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Synthesis of 9,10‐Bis(organochalcogenyl)phenanthrenes by Cyclization of (Biphenyl‐2‐alkyne)chalcogenides

Hellwig,

Goulart,

Guedes

et al. 2024

Asian J Org Chem

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A regioselective, operationally simple and scalable protocol was developed for the synthesis of 9,10‐bis(organochalcogenyl)phenanthrenes and seleno‐spiro[cyclohexane‐1,1'‐indene]‐2,5‐dien‐4‐ones through the cyclization of (biphenyl‐2‐alkyne)chalcogenides. The reaction occurs in the presence of diorganyl diselenides, Oxone® as a green oxidizing agent, and acetonitrile at 80 °C. In this study, 20 compounds were obtained in yields of up to 97% and in short reaction times (1‐4 h).

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Nitrogen-doped carbon layer encapsulating NiFeP nanosheet arrays as high-performance electrocatalyst for oxygen evolution reaction

Wang,

Shi,

Zhou

et al. 2024

Journal of Alloys and Compounds

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Controllable cyclization of alkynyl thioethersviaBrønsted acid-catalyzed dearomatization

Abstract: An efficient Brønsted acid-catalyzed formal alkyne hydroarylation of phenol-alkynyl thioethers via dearomatization and rearrangement is described. This protocol enables the practical and atom-economic synthesis of valuable phenanthrols in generally excellent...

Cited by 5 publications

References 71 publications

Copper‐Catalyzed Dearomative Cyclization of Indolyl Ynamides for Synthesis of Pentacyclic Spiroindolines

Copper‐Catalyzed Dearomative Cyclization of Indolyl Ynamides for Synthesis of Pentacyclic Spiroindolines

Synthesis of 9,10‐Bis(organochalcogenyl)phenanthrenes by Cyclization of (Biphenyl‐2‐alkyne)chalcogenides

Nitrogen-doped carbon layer encapsulating NiFeP nanosheet arrays as high-performance electrocatalyst for oxygen evolution reaction

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