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. 2020 Jan 7;59(2):653-657.
doi: 10.1002/anie.201909557. Epub 2019 Nov 18.

Palladium-Catalyzed [2+2+1] Spiroannulation via Alkyne-Directed Remote C-H Arylation and Subsequent Arene Dearomatization

Zhijun Zuo  1 , Jing Wang  1 , Jingjing Liu  1 , Yaoyu Wang  1 , Xinjun Luan  1
Affiliations

Palladium-Catalyzed [2+2+1] Spiroannulation via Alkyne-Directed Remote C-H Arylation and Subsequent Arene Dearomatization

Zhijun Zuo et al. Angew Chem Int Ed Engl. .

Abstract

Palladium-catalyzed alkene-directed cross-coupling of aryl iodide with another aryl halide through C-H arylation opens a unique avenue for unsymmetrical biaryl-derived molecules. However, homo-coupling of aryl iodides often erodes the overall synthetic efficiency. Reported herein is a highly chemoselective Pd0 -catalyzed alkyne-directed cross-coupling of aryl iodides with bromophenols, which was subsequently followed by phenol dearomatization to furnish a very attractive [2+2+1] spiroannulation. Notably, possible homo-coupling of aryl iodides was not observed at all. Mechanistic studies indicated that a five-membered aryl/vinyl palladacycle most likely accounts for promoting the key step of biaryl cross-coupling.

Keywords: C−H activation; aryl halides; cross-coupling; dearomatization; palladacycles.

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References

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