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Build-Up of Double Carbohelicenes Using Nitroarenes: Dual Role of the Nitro Functionality as Activation and Leaving Group

Abstract

The construction of double carbohelicenes is a highly fascinating yet challenging work. Disclosed herein is a streamlined and simplified synthetic route to double carbohelicenes starting from nitroarenes through sequential nitro-activated ortho-C−H arylation, denitrative alkenylation and intramolecular cyclodehydrogenation. In this synthetic strategy, the nitro group plays a dual role including as a leaving group for the denitrative alkenylation and as an activating group for ortho-C−H arylation, which is distinct from those of aryl halides in conventional coupling reaction. In this work, the palladium-catalyzed Heck-type alkenylation of nitroarenes has been presented, in which the conventionally inert Ar−NO2 bond is cleaved. This work provides a novel synthetic strategy for polycyclic aromatic hydrocarbons (PAHs).

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Article information


Submitted
11 Apr 2020
Accepted
23 Jun 2020
First published
25 Jun 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Accepted Manuscript
Article type
Edge Article

Build-Up of Double Carbohelicenes Using Nitroarenes: Dual Role of the Nitro Functionality as Activation and Leaving Group

F. Zhou, F. Zhou, R. Su, Y. Yang and J. You, Chem. Sci., 2020, Accepted Manuscript , DOI: 10.1039/D0SC02058C

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