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
, pp. 7523-7530.
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 |
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Date Type: | Publication |
Status: | Published |
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: | 26 Nov 2020 15:11 |
URI: | http://orca-mwe.cf.ac.uk/id/eprint/135092 |
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