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


Citation
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


Description

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.


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