Synthesis of Benzylic Quaternary Centers via Arylation with Aryl(TMP)iodonium Salts
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Updated: Oct 25, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Joseph Hatton1, Nikhil Bonagiri1, David R Stuart1
1Department of Chemistry, Portland State University, Portland, Oregon97201, United States.
Abstract:
Benzylic quaternary centers are important molecular scaffolds, but their synthesis via the arylation of tertiary malonates remains underdeveloped. Herein, we exploit the metal-like reactivity of diaryliodonium salts to realize this transformation. Design of experiment (DoE) is used to discover mild conditions with a broad scope of aryl electrophiles in high yields, including the coupling of electron-rich aryl rings. Telescoping diaryliodonium synthesis and C-C coupling into a one-pot sequence opens a new possibility for C-C coupling with aryl iodides.
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