Copper-catalyzed intermolecular formal [4 + 1] annulation of 1,5-diynes with benzocyclobutenones

Jia-Cheng Li; Tian-Qi Hu; Zhou Xu; Bo Zhou; Long-Wu Ye

Tetrahedron Chem (Dec 2024)

Copper-catalyzed intermolecular formal [4 + 1] annulation of 1,5-diynes with benzocyclobutenones

Jia-Cheng Li,
Tian-Qi Hu,
Zhou Xu,
Bo Zhou,
Long-Wu Ye

Affiliations

Jia-Cheng Li: State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China
Tian-Qi Hu: State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China
Zhou Xu: Jiangsu Key Laboratory of New Drug Research and Clinical Pharmacy, School of Pharmacy, Xuzhou Medical University, Xuzhou, 221004, China; Corresponding author.
Bo Zhou: State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China
Long-Wu Ye: State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China; State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China; Corresponding author. State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.

Journal volume & issue: Vol. 12
p. 100090

Abstract

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The one-carbon ring expansion of benzocyclobutenones is an efficient methodology for the assembly of cyclic ketones. However, hazardous reagents or noble metal catalysts are frequently required. Herein, we disclose a copper-catalyzed intermolecular formal [4 + 1] annulation of 1,5-diynes with benzocyclobutenones, allowing the practical and atom-economical construction of diverse pyrryl 1-indanones in generally good yields under mild reaction conditions. This reaction represents an important advancement in the ring expansion of benzocyclobutenones via vinyl cation pathway.

Published in Tetrahedron Chem

ISSN: 2666-951X (Online)
Publisher: Elsevier
Country of publisher: United Kingdom
LCC subjects: Science: Chemistry: Organic chemistry
Website: https://www.journals.elsevier.com/tetrahedron-chem

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