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Mini-Reviews in Organic Chemistry

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ISSN (Online): 1875-6298

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Review Article

Transition Metal-catalyzed Regioselective Direct C-H Arylations Using Quinone Diazide as Arylating Agent: A Mini Review

Author(s): Partha Pratim Das and Debapratim Das*

Volume 20, Issue 5, 2023

Published on: 30 August, 2022

Page: [494 - 508] Pages: 15

DOI: 10.2174/1570193X19666220531153554

Price: $65

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Abstract

Quinone diazides are a class of diazo compounds, having a planar six-membered ring system with diazo, carbonyl, and alkene groups in conjugation. It has been used in optical, electronic, and polymer materials. In the last few years, these diazo compounds explored various rearrangements reactions and insertion reactions via the formation of metallo-carbenoids. Recently, it has been used to incorporate phenol moieties into hydrocarbons or arene/heteroarenes systems via transition metalcatalyzed C-H bond activation. The reactions proceed via C-H bond insertion or migratory insertion of metal-carbenes. In many cases, the site-selectivities were obtained by the guidance of various directing groups (removable or non-removable). At the same time, several asymmetric approaches were also studied to incorporate phenol derivatives to arenes/heteroarenes furnishing compounds showing axial chirality with high stereoselectivity. This review will mainly focus on directed regioselective arylation with quinone diazides under transition metal catalysis through C-H bond activation.

Keywords: C-H bond activation, quinone diazides, carbene, arylation, transition metal, spiroannulation, asymmetric arylation.

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