142020 - Triarylborane catalysed N-alkylation of amines with aryl esters.pdf (3.71 MB)
Triarylborane catalysed N-alkylation of amines with aryl esters
journal contribution
posted on 2023-05-20, 19:45 authored by Nori, V, Dasgupta, A, Rasool BabaahmadiRasool Babaahmadi, Carlone, A, Alireza AriafardAlireza Ariafard, Melen, RLThe 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.
Funding
Australian Research Council
University of Wollongong
History
Publication title
Catalysis Science & TechnologyVolume
10Issue
22Pagination
7523-7530ISSN
2044-4761Department/School
School of Natural SciencesPublisher
Royal Soc ChemistryPlace of publication
United KingdomRights statement
Copyright 2020 the authors and The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 (CC BY) Unported LicenceRepository Status
- Open