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

Shugao Zhu; Wenliang Huang; Shihan Liu; Rongjing Yu; Yufeng Ma; Hong Wang; Rui Zhang; Bin Liu; Yu Lan; Ruwei Shen

doi:10.1039/D4CC00999A

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

Shugao Zhu,

*^a Wenliang Huang,^a Shihan Liu,

^b Rongjing Yu,^a Yufeng Ma,^a Hong Wang,^a Rui Zhang,^a Bin Liu,

^a Yu Lan

*^bc and Ruwei Shen

^d

Author affiliations

* Corresponding authors

^a School of Chemistry and Chemical Engineering, Nanchang University, Nanchang 330031, China
E-mail: shugaozhu@ncu.edu.cn

^b School of Chemistry and Chemical Engineering, Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing 400030, China
E-mail: lanyu@cqu.edu.cn

^c College of Chemistry and Institute of Green Catalysis, Zhengzhou University, Zhengzhou 450001, China

^d State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University, Nanjing 211800, China

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.

Chemical Communications

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

Abstract

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

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