Copper-catalyzed remote C-H arylation of polycyclic aromatic hydrocarbons (PAHs).

Anping Luo,Zhangyi Fu,Jingsong You,Di Wu,Jingbo Lan,Min Zhang

doi:10.3762/bjoc.16.49

Abstract

The regioselective C–H arylation of substituted polycyclic aromatic hydrocarbons (PAHs) is a desired but challenging task. A copper-catalyzed C7–H arylation of 1-naphthamides has been developed by using aryliodonium salts as arylating reagents. This protocol does not need to use precious metal catalysts and tolerates wide variety of functional groups. Under standard conditions, the remote C–H arylation of other PAHs including phenanthrene-9-carboxamide, pyrene-1-carboxamide and fluoranthene-3-carboxamide has also accomplished, which provides an opportunity for the development of diverse organic optoelectronic materials.

Highlights

Polycyclic aromatic hydrocarbons (PAHs) with rigid planar structure, such as naphthalene, phenanthrene, pyrene and their derivatives, can usually emit relatively strong fluorescence, and have been widely applied in many scientific areas including chemistry, biomedicine and materials science [1-6]
As a component part of our ongoing research on direct C–H bond functionalization [20,27-29], we represent a copper-catalyzed remote C–H arylation of PAHs with aryliodonium salts as arylating reagents (Scheme 1). This protocol is compatible with different PAH substrates including 1-naphthamides, phenanthrene-9-carboxamide, pyrene-1-carboxamide and fluoranthene-3-carboxamide, which provides an opportunity for the development of diverse organic photoelectrical materials
Our investigation commenced with the reaction between N-(tert-butyl)-1-naphthamide (1a) and mesityl(phenyl)iodonium triflate (2a, for detailed optimization, see Table S1, Supporting Information File 1)

Summary

Introduction

Polycyclic aromatic hydrocarbons (PAHs) with rigid planar structure, such as naphthalene, phenanthrene, pyrene and their derivatives, can usually emit relatively strong fluorescence, and have been widely applied in many scientific areas including chemistry, biomedicine and materials science [1-6]. As a component part of our ongoing research on direct C–H bond functionalization [20,27-29], we represent a copper-catalyzed remote C–H arylation of PAHs with aryliodonium salts as arylating reagents (Scheme 1). This protocol is compatible with different PAH substrates including 1-naphthamides, phenanthrene-9-carboxamide, pyrene-1-carboxamide and fluoranthene-3-carboxamide, which provides an opportunity for the development of diverse organic photoelectrical materials.

Results

Conclusion