The Diaryliodonium(III) Salts Reaction With Free-Radicals Enables One-Pot Double Arylation of Naphthols

Frontiers in Chemistry
Yuvraj SatkarCésar R Solorio-Alvarado

Abstract

The chemoselective reaction of the C- followed by the O-centered naphthyl radicals with the more electron-deficient hypervalent bond of the diaryliodonium(III) salts is described. This discovered reactivity constitutes a new activation mode of the diaryliodonium(III) salts which enabled a one-pot doubly arylation of naphthols through the sequential C s p 2 - C s p 2 /O- C s p 2 bond formation. The naphthyl radicals were generated in the reaction by the tetramethylpiperidinyl radical (TMP·) which resulted from the homolytic fragmentation of the precursor TMP2O. Experimental and DFT calculations provided a complete panorama of the reaction mechanism.

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Citations

Nov 3, 2021·The Journal of Organic Chemistry·Neha ChalotraBhahwal Ali Shah

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Methods Mentioned

BETA
column chromatography

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