Teitl: 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

Hawliau Mynediad: Darperir Data dan drwydded Creative Commons Attribution (CC BY 4.0)
Dull Mynediad: I anfon cais i gael y data hwn, ebostiwch opendata@caerdydd.ac.uk

Crewyr y Set Ddata o Brifysgol Caerdydd

Manylion y Set Ddata
Cyhoeddwr: Cardiff University
Dyddiad (y flwyddyn) pryd y daeth y data ar gael i'r cyhoedd: 2020
Dyddiad dechrau creu'r data: 01.09.2017
Dyddiad gorffen creu'r data: 18.09.2020
Fformat y data: .jpeg, .cif, .pdf
Meddalwedd ofynnol: NMR and Xray data visualisation software
DOI: 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.

Prosiectau Cysylltiedig

Diweddarwyd y tro diwethaf ar 2020-22-09 am 15:05