Title: Triarylborane Catalysed N-Alkylation of Amines with Aryl Esters - data

Nori V, Dasgupta A, Babaahmadi R, et al. (2020). Triarylborane Catalysed N-Alkylation of Amines with Aryl Esters - data. Cardiff University. http://doi.org/10.17035/d.2020.0117003506

Access Rights: Data is provided under a Creative Commons Attribution (CC BY 4.0) licence

Access Method: Click to email a request for this data to opendata@cardiff.ac.uk

Cardiff University Dataset Creators

Dataset Details

Publisher: Cardiff University

Date (year) of data becoming publicly available: 2020

Coverage start date: 01/09/2017

Coverage end date: 18/09/2020

Data format: .jpeg, .cif, .pdf

Software Required: NMR and Xray data visualisation software

DOI : 10.17035/d.2020.0117003506

DOI URL: http://doi.org/10.17035/d.2020.0117003506


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, carbazoles, 1H-indoles, and 1H-pyrroles 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 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.

The dataset includes experimental procedures, NMR and Xray data.

Related Projects

Last updated on 2021-24-08 at 11:39