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Triarylborane catalysed n-alkylation of amines with aryl esters

Nori, Valeria, Dasgupta, Ayan, Babaahmadi, Rasool, Carlone, Armando, Ariafard, Alireza and Melen, Rebecca 2020. Triarylborane catalysed n-alkylation of amines with aryl esters. Catalysis Science and Technology 10.1039/D0CY01339K

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Abstract

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
Date Type: Published Online
Status: In Press
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Publisher: Royal Society of Chemistry
ISSN: 2044-4753
Funders: EPSRC
Date of First Compliant Deposit: 24 September 2020
Date of Acceptance: 15 September 2020
Last Modified: 14 Oct 2020 13:05
URI: http://orca.cf.ac.uk/id/eprint/135092

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