Issue 44, 2024

Synthesis of benzooxepane-fused cyclobutene derivatives via Pd-catalyzed cascade reactions of haloarenes and diynylic ethers

Abstract

A tandem palladium-catalyzed Sonogashira coupling, propargyl–allenyl isomerization, and [2+2] cycloaddition sequence between electron-deficient haloarenes and 1,8-diynylic ethers is developed. The reaction shows good functional tolerance and proceeds under mild conditions to provide a new profile of benzooxepane-fused cyclobutene derivatives in moderate to high yields with high selectivity. The reaction mechanism is validated both by experimental studies and DFT calculations.

Graphical abstract: Synthesis of benzooxepane-fused cyclobutene derivatives via Pd-catalyzed cascade reactions of haloarenes and diynylic ethers

Supplementary files

Article information

Article type
Communication
Submitted
01 Mar 2024
Accepted
06 May 2024
First published
10 May 2024

Chem. Commun., 2024,60, 5707-5710

Synthesis of benzooxepane-fused cyclobutene derivatives via Pd-catalyzed cascade reactions of haloarenes and diynylic ethers

S. Zhu, W. Huang, S. Liu, R. Yu, Y. Ma, H. Wang, R. Zhang, B. Liu, Y. Lan and R. Shen, Chem. Commun., 2024, 60, 5707 DOI: 10.1039/D4CC00999A

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