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Triarylborane catalysed N-alkylation of amines with aryl esters


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Nori, V, Dasgupta, A, Babaahmadi, R, Carlone, A, Ariafard, A ORCID: 0000-0003-2383-6380 and Melen, RL 2020 , 'Triarylborane catalysed N-alkylation of amines with aryl esters' , Catalysis Science & Technology, vol. 10 , 7523–7530 , doi: 10.1039/d0cy01339k.

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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.

Item Type: Article
Authors/Creators:Nori, V and Dasgupta, A and Babaahmadi, R and Carlone, A and Ariafard, A and Melen, RL
Keywords: aryl esters, metal-free catalysis, DFT, mechanistic study
Journal or Publication Title: Catalysis Science & Technology
Publisher: Royal Soc Chemistry
ISSN: 2044-4761
DOI / ID Number: 10.1039/d0cy01339k
Copyright Information:

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

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