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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

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Dearomatization [4+2] Cycloaddition of Nonactivated Benzene Derivatives

Junjian Wang¹, Haotian Luo¹, Xinghua Wang¹

¹College of Chemistry, Green Catalysis Center, International Phosphorus Laboratory, International Joint Research Laboratory for Functional Organophosphorus Materials of Henan Province, Zhengzhou University, Zhengzhou 450001, P. R. China.

Organic Letters

|June 10, 2022

Abstract:

Dearomatization reactions have recently emerged as a powerful tool for the rapid buildup of molecular complexity. Here, an unparalleled thermal dearomatization [4+2] cycloaddition reaction between benzene derivatives and a 2H-phosphindole tungsten complex was reported. The unique reactivity of the in situ-generated 2H-phosphindole complex toward benzene was revealed by density functional theory calculations. We thus provide new insights into the dearomatization of nonactivated arenes and pave the way for the manipulation of the dearomatization for further applications.

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