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Triarylborane catalysed N-alkylation of amines with aryl esters

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Abstract

The ability of halogenated triarylboranes to accept a lone pair of electrons from donor substrates renders them excellent Lewis acids which can be exploited as a powerful tool in organic synthesis. Tris(pentafluorophenyl)borane has successfully demonstrated its ability to act as a metal-free catalyst for an ever-increasing range of organic transformations. Herein we report the N-alkylation reactions of a wide variety of amine substrates including diarylamines, N-methylphenyl amines, and carbazoles with aryl esters using catalytic amounts of B(C6F5)3. This mild reaction protocol gives access to N-alkylated products (35 examples) in good to excellent yields (up to 95%). The construction of a C–N bond at the propargylic position has also been demonstrated to yield synthetically useful propargyl amines. On the other hand, unsubstituted 1H-indoles and 1H-pyrroles at the C3/C2 positions afforded exclusively C–C coupled products. Extensive DFT studies have been employed to understand the mechanism for this transformation.

Graphical abstract: Triarylborane catalysed N-alkylation of amines with aryl esters

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Article information


Submitted
03 Jul 2020
Accepted
15 Sep 2020
First published
16 Sep 2020

This article is Open Access

Catal. Sci. Technol., 2020, Advance Article
Article type
Paper

Triarylborane catalysed N-alkylation of amines with aryl esters

V. Nori, A. Dasgupta, R. Babaahmadi, A. Carlone, A. Ariafard and R. L. Melen, Catal. Sci. Technol., 2020, Advance Article , DOI: 10.1039/D0CY01339K

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