Triarylborane catalysed n-alkylation of amines with aryl esters

Nori, Valeria, Dasgupta, Ayan, Babaahmadi, Rasool, Carlone, Armando, Ariafard, Alireza and Melen, Rebecca ORCID: https://orcid.org/0000-0003-3142-2831 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
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:	05 May 2023 23:54
URI:	https://orca.cardiff.ac.uk/id/eprint/135092

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