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Triarylborane catalysed N-alkylation of amines with aryl esters

Citation

Nori, V and Dasgupta, A and Babaahmadi, R and Carlone, A and Ariafard, A and Melen, RL, Triarylborane catalysed N-alkylation of amines with aryl esters, Catalysis Science & Technology, 10, (22) pp. 7523-7530. ISSN 2044-4761 (2020) [Refereed Article]


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Copyright 2020 the authors and The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 (CC BY) Unported Licence

DOI: doi:10.1039/d0cy01339k

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 CN 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 CC coupled products. Extensive DFT studies have been employed to understand the mechanism for this transformation.

Item Details

Item Type:Refereed Article
Keywords:aryl esters, metal-free catalysis, DFT, mechanistic study
Research Division:Chemical Sciences
Research Group:Organic chemistry
Research Field:Physical organic chemistry
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the chemical sciences
UTAS Author:Babaahmadi, R (Mr Rasool Babaahmadi)
UTAS Author:Ariafard, A (Associate Professor Alireza Ariafard)
ID Code:142020
Year Published:2020
Funding Support:Australian Research Council (DP180100904)
Deposited By:Chemistry
Deposited On:2020-12-08
Last Modified:2021-07-05
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