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Gold-catalyzed intermolecular [4+1] spiroannulation <i>via</i> site-selective aromatic C(sp<sup>2</sup>)–H functionalization and dearomatization of phenol derivatives

Yongfeng Li, Zhiqiong Tang, Junliang Zhang, Lu Liu

2020Chemical Communications36 citationsDOIOpen Access PDF

Abstract

Herein, we have developed a novel and simple protocol to realize the C-H bond functionalization/dearomatization of naphthols and phenols with ortho-alkynylaryl-α-diazoesters under gold(i) catalysis. In this protocol, various spirocyclic molecules could be obtained in good yields with excellent chemo- and regio-selectivity and moderate to good diastereoselectivity.

Topics & Concepts

CatalysisSurface modificationIntermolecular forceChemistryPhenolMedicinal chemistryStereochemistryCombinatorial chemistryOrganic chemistryMoleculePhysical chemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions
Gold-catalyzed intermolecular [4+1] spiroannulation <i>via</i> site-selective aromatic C(sp<sup>2</sup>)–H functionalization and dearomatization of phenol derivatives | Litcius