Ligand and counteranion enabled regiodivergent C-H bond functionalization of naphthols with α-aryl-α-diazoesters

Chemical Science
Zhunzhun YuJunliang Zhang

Abstract

Here, an unprecedented ligand and counteranion-controlled and site-selectivity switchable direct C-H bond functionalization of unprotected naphthols with α-aryl-α-diazoesters was developed. In this transformation, site selectivities are realized by turning on/off the coordination between metal complexes and hydroxy groups. The preliminary mechanism revealed that the interaction between the hydroxy group and gold catalyst plays a key role in switching the site-selectivity of gold-carbene. This protocol potentially provides a novel design for C-H bond functionalization.

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Citations

Feb 19, 2020·Angewandte Chemie·Natalie Holmberg-DouglasDavid A Nicewicz
Apr 25, 2020·Chemistry : a European Journal·Juan Diego PizarroPedro J Pérez
Feb 9, 2021·Chemical Reviews·Chetan C ChintawarNitin T Patil
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Apr 28, 2021·Chemistry : a European Journal·Chandrasekar PraveenVéronique Michelet
Jun 23, 2021·Organic & Biomolecular Chemistry·Zhiqiong TangLu Liu
Jun 25, 2021·Chemical Science·Pu ChenMichal Szostak
Aug 25, 2020·The Journal of Organic Chemistry·Feifei HeRene M Koenigs
Oct 26, 2021·Chemistry : a European Journal·Mojtaba Hajiloo ShayeganXin Cui

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Methods Mentioned

BETA
NMR
X-ray

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