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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
Authors/Creators:	Nori, V and Dasgupta, A and Babaahmadi, R and Carlone, A and Ariafard, A and Melen, RL
Keywords:	aryl esters, metal-free catalysis, DFT, mechanistic study
Journal or Publication Title:	Catalysis Science & Technology
Publisher:	Royal Soc Chemistry
ISSN:	2044-4761
DOI / ID Number:	10.1039/d0cy01339k
Copyright Information:	Copyright 2020 the authors and The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 (CC BY) Unported Licence
Related URLs:	Google Scholar: Ariafard, A UTAS Profile: Ariafard, A
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