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Issue 13, 2021

Palladium-catalyzed C8–H arylation and annulation of 1-naphthalene carboxylic acid derivatives with aryl iodides

Author affiliations

Abstract

The discovery of a concise route enabling site-selective arylation of polycyclic aromatic hydrocarbons (PAHs) with easily available aryl sources is an appealing yet challenging task toward the bottom-up preparation of π-extended PAHs. Disclosed herein is a palladium-catalyzed C8–H arylation of 1-naphthoic acid derivatives with aryl iodides in a low reactant molar ratio via an electrophilic aromatic substitution (SEAr) process. In addition, a C8–H annulation protocol is developed to rapidly assemble benzanthrones by simply switching the solvent to 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP).

Graphical abstract: Palladium-catalyzed C8–H arylation and annulation of 1-naphthalene carboxylic acid derivatives with aryl iodides

Supplementary files

Article information


Submitted
17 Mar 2021
Accepted
08 Apr 2021
First published
14 Apr 2021

Org. Chem. Front., 2021,8, 3274-3279
Article type
Research Article

Palladium-catalyzed C8–H arylation and annulation of 1-naphthalene carboxylic acid derivatives with aryl iodides

M. Zhang, Z. Fu, A. Luo, X. Pu, M. Wang, Y. Huang, Y. Yang and J. You, Org. Chem. Front., 2021, 8, 3274 DOI: 10.1039/D1QO00428J

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