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Access to the most sterically crowded anilines via non-catalysed C–C coupling reactions

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Abstract

Variously substituted 2,6-bis(1,1-diarylethyl)anilines and 2,6-bis(trityl)anilines were prepared by a three-step high-yield process. Dimethyl-2-aminoisophtalate was modified by reaction with arylmagnesium bromides, and the hydroxy-derivatives obtained were etherified. Under the non-catalysed C–C coupling protocol, the formed bis[methyl(methoxy)diaryl]anilines react with various Grignard reagents to give highly substituted products. The buried volumes around the central nitrogen atom of the prepared compounds exceed the parameters for the known most sterically hindered anilines by about 20%.

Graphical abstract: Access to the most sterically crowded anilines via non-catalysed C–C coupling reactions

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Article information


Submitted
06 Dec 2019
Accepted
21 Jan 2020
First published
21 Jan 2020

This article is Open Access

Chem. Commun., 2020, Advance Article
Article type
Communication

Access to the most sterically crowded anilines via non-catalysed C–C coupling reactions

J. Vrána, M. A. Samsonov, V. Němec and A. Růžička, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC09497K

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